Pyrrolidine carboxylic acid

Pyrrolidine-3-carboxylic acid, 4-oxo-synthesis, 4, 518 Pyrrolidinediones polymerization, I, 271-272 Pyrrolidinediones, tetramethyl-... 

Enantiopure (R)- and (S)-nipecotic acid (Nip) derivatives 64 were obtained following classical resolution of ethyl nipecotate with either enantiomer of tartaric acid and successive recrystallization of the corresponding salts [153, 154, 156] or by resolution of racemic nipecotic acid with enantiomerically pure camphorsul-fonic acid [154]. N-Boc protected pyrrolidine-3-carboxylic acid (PCA) 65 for the synthesis of homo-ohgomers [155] was prepared by GeUman from trans-4-hydroxy-L-prohne according to a known procedure [157]. 

Figure 15.1 (1 R,2S)-2-Aminocyclopentanecarboxylic acid (cispentacin), (R)-pyrrolidine-3-carboxylic acid (P proline), and (7R,3S)-3-aminocyclopentanecarboxylic acid.

The expected synthesis of a-S-diaminovalerianic acid, which was attempted by Willstatter in 1900, by the action of ammonia upon a-B-dibromovalerianic acid, led to the synthesis of a-pyrrolidine-carboxylic acid, and only in the following year was the synthesis of this important naturally occurring diamino acid accomplished by E. Fischer. He made use of Gabriel s phthalimide method with a slight modification and obtained ornithine by the following series of reactions —... 

It was also synthesised by E. Fischer in 1901 from 7-phthalimido-propylmalonic ester which he employed in the preparation of ornithine. The bromine derivative of this compound when treated with ammonia gave a complex mixture of products which after hydrolysis by hydrochloric acid at 100° C. gave phthalimide and a-pyrrolidine carboxylic acid —... 

The question at once arose whether this a-pyrrolidine carboxylic acid, or a-proline as Fischer termed it in 1904, was a primary product or a secondary product formed by the action of mineral acids upon other products, but its formation by hydrolysis by alkali and by the action of pepsin followed by trypsin decided that it was a primary product and therefore one of the units of the protein molecule. Sorensen, in 1905, suggested that it might arise from an a-amino-S-oxyvalerianic acid which he synthesised, but the fact that this amino acid has not yet been obtained by hydrolysis of protein and the above facts seem to exclude this possibility. 

In 1902 E. Fischer isolated a compound of the empirical formula CgHjOsN from the hydrolysis products of gelatin. From its composition he supposed that it was an oxy-derivative of pyrrolidine carboxylic acid, and this was proved by its reduction to proline with hydriodic acid. 

BMIm]BF4 BMImCl [BMIm]PF6 CCS ecu [Choline] [Pro] 1 -butyl-3-methyl-imidazolium tetrafluoroborate 1 -butyl-3-methyl-imidazolium chloride 1 -butyl-3-methyl-imidazolium hexafluorophosphate CO2 capture and storage/sequestration CO2 capture and utilization (2-hydroxyethyl)-trimethyl-ammonium (iS )-2-pyrrolidine-carboxylic acid salt... 

Table 2.12 ont/ -Mannich-type reactions of aldehyde donors and N-PMP-protected glyoxylate imine catalyzed by (3/ ,5/ )-5-methyl-3-pyrrolidine-carboxylic acid (13) [73]. 

R)-(+)-2-(Diphenylhydroxymethyl)-N-(tert-butoxycarbonyl)pyrrolidine 1-Pyrrolidine-carboxylic acid, 2-(hydroxydiphenylmethyl)-, 1,1-dimethylethyl ester, (R)- (12) (137496-68-5)... 

C. Preparation of 2-oxo-1 -phenyl- 3-pyrrolidine carboxylic acid (3). To 1.70 g (10 mmol) of spiroacylal 2 was added 2.79 g (3 mmol) of aniline. The mixture became a homogeneous orange solution after 15 min and was allowed to stir at room temperature for 12 hr. The resulting crystalline mass was diluted with 150 mL of chloroform, washed three times with 10 mL of aqueous 10% hydrochloric acid, washed once with 20 mL of brine, dried (MgS04), and decolorized with a small amount of activated carbon. Concentration of the organic layer by rotary evaporation gave 5.27 g of a brown residue, which was recrystallized from chloroform-hexane to afford 4.86-5.07 g (79-82%) of the pyrrolidinone 3 as white crystals, mp 146-148°C (dec) (Note 4). 

Proline, C4H8N—COOH, a-Pyrrolidine Carboxylic Acid This compound is not a simple amino acid but is a carboxyl derivative of a five membered cyclic compound, containing an (—NH—) group, known as pyrrolidine (p. 194 and Part II). 

Oxy-proline, (C4H7(OH)N)—COOH, a-(Hydroxy Pyrrolidine) Carboxylic Acid. As its name indicates oxy-proline is an hydroxy derivative of proline. The position of the hydroxyl group in the pyrrolidine ring is not known. 

Proline.—Two of the amino acids obtained as hydrolytic cleavage products of proteins are derivatives of pyrrolidine. They are proline and oxyproline (p. 392). Proline is a//>/fa-pyrrolidine carboxylic acid. 

Fig. 11.12 Two examples of cis Xaa-Pro mimetics (40) (6S,8aR)-6-amino-5-oxo-octahydroindolizine-8a-carboxylic acid was obtained in in good yields and enantiomerically homogeneous form [125-129]. The compound (S)-l-((S,Z)-2-aminohept-4-enoyl)pyrrolidine-carboxylic acid (41) was derived from MD simulations and synthesized as enantiomerically pure compound by Grubb s ring-closing olefin metathesis [130].

The synthesis of the penicillin bulgecin (136) hybrid is achieved from benzhydryl 6-aminopenicillanate (134) via coupling with pyrrolidine carboxylic acid ester 135 using DEPC. 

Glutamine cyclizes to form pyrrolidine carboxylic acid (shown in Figure 4.3) ... 

Synonyms. rans-l-Acetyl-4-hydroxy-L-proline l-Acetyl-4-hydroxy-2-pyrrolidine carboxylic acid. 

CAS 51-35-4 EINECS/ELINCS 200-091-9 Synonyms Hydroxyproline (INCI) 4-Hydroxy-L-proline 4-Hydroxy-2-pyrrolidine carboxylic acid Hyp L-Proline, 4-hydroxy-... 

Synonyms Pro Proline (INCI) 2-Pyrrolidine carboxylic acid Pyrrolidine-2-carboxylic acid... 

H-Pyrrole-2,5-dione, 1,T-(phenylene) bis-. See m-Phenylenedimaleimide IH-Pyrrole, 1-(2-furanylmethyl)- Pyrrole, 1-furfuryl-. See 1-Furfuryl-1H-pyrrole 2-Pyrrolidine carboxylic acid Pyrrolidine-2-carboxylic acid. SeeL-Proline 2,5-Pyrrolidinedione. See Succinimide... 

Several syntheses have appeared in which pyrrolidine carboxylic acids other than proline have been prepared. Refunctionalization of proline is an also excellent route to "non-proline" amino acids, however, because of the ready availability of proline and its derivatives. Proline (7.250) was converted to aldehyde 7.25J by standard procedures, and Wittig olefination lej to 7.252.133 In an interesting transforma-... 

Scheme 17.14 Example of cmti-selective Mannich reaction between N-p-methoxyphenyl (PMP) protected imine catalyzed by 5-methyl-3-pyrrolidine carboxylic acid.

Anti-selective Mannich reactions have been developed using (R)-3-pyrrolidine-carboxylic acid (75) or primary amine-containing amino acid 21 these catalysts were designed through consideration of mechanism and transition state models. 

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