Propionic acid, 2-phenyl-2- synthesis

In 1909, Thiele and Landers reported the synthesis of p- (3-methoxy-isoxazol-5-yl)-propionic acid (77), from the corresponding chloride or bromide (76). In 1961, a similar reaction was reported for 3-chloro-5-arylisoxazoles, enabling the synthesis of 3-hydroxy-5-phenyl-... 

The reaction of potassium 3-amino-4-oxo-3,4-dihydroquinazoline-2-thiolate 62 with a-bromophenylacetic acid 63 resulted in the formation of (3-amino-4-oxo-3,4-dihydroquinazolin-2-ylsulfanyl)-phenyl-acetic acid methyl ester 64 which on alkali treatment and subsequent acidification resulted in the synthesis of 2-phenyl- 1-thia-4,4a,9-triaza-anthracene-3,10-dione 65 <1999JCR(S)86>. Similarly, the reaction of potassium 3-amino-5,6-dimethyl-4-oxo-3,4,4a,7a-tetrahydrothieno[2,3- pyrimidine-2-thiolate 66 with a-bromo-ester 67 resulted in the formation of 2-(3-amino-5,6-dimethyl-4-oxo-3,4,4a,7a-tetrahydrothieno[2,3- / pyrimidin-2-ylsulfanyl)-propionic acid ethyl ester 68. Subsequent treatment with alkali followed by acidification resulted in the formation of 2,3,7-trimethyl-3a,9a-dihydro-l,8-dithia-4a,5,9-triazacyclopenta[ ]naphthalene-4,6-dione 69 <2000JHC1161>... 

Some new approaches to the synthesis of pyridazino[3,4-c]pyridazines have been described. The pyrazolopyridazino[3,4-c]pyridazines (13 R = OMe, Me) and (14) are prepared by the reaction of /i-aroyl-a-(3-methyl-5(4//)-oxo-l-phenyl-4-pyrazolyl)propionic acid (12) with hydrazine or phenyl-hydrazine in butanol (Scheme 2) <90IJC(B)72>. 

Scheme 66 Synthesis of 2-hetero-(benzisothiazol-3-yl)(3-phenyl)propionic acids...

Suh et al.65 have reported a formal total synthesis of Mansonone F and this is described in Scheme 12. 5-Methoxy-a-tetralone (127) was converted to 1-methyl-5-hydroxy-naphthalene (128) by the standard organic reactions. Treatment of (128) with phenyl boronic acid, paraformaldehyde and propionic acid followed by catalytic hydrogenation yielded compound (129). This on alkylation gave the compound (130) which on alkaline hydrolysis was converted to acid. The acid halide underwent intramolecular Friedal-Crafts acylation affording an intermediate (131) whose transformation to Mansonone F has been accomplished by Best and Wege.59... 

Amino cyanides are obtained by the action of ammonia and hydrocyanic acid, or of ammonium chloride and sodium cyanide, on aldehydes, or alternatively from cyanohydrins and ammonia. They are best hydrolysed by concentrated hydrochloric acid, the resulting amino acids being then obtained as hydrochlorides, whence the free amino acids can be liberated by means of lead monoxide, ammonia, or pyridine. For a critical consideration of the hydrolysis of amino cyanides see Cocker and Lapworth.632 The synthesis of DL-alanine has been detailed twice.780 633 That of racemic ac-amino-ac-phenyl-propionic acid from acetophenone, sodium cyanide, and ammonium chloride by way of the amino cyanide was worked out by Steiger.634 /9-Alanine is obtained in 85-90% yield when 3-aminopropionitrile is added to aqueous barium hydroxide at 90-95° during 40 min and kept at that temperature for a further 40 min.635... 

Patel RN, Banerjee A, Howell JM, McNamee CG, Brzozowski D, Nanduri V, Thottathil JK, Szarka LJ (1995) Stereoselective Microbial Reduction of 2-Keto-3-(N-benzoylamino)-3-phenyl Propionic Acid Ethyl Ester Synthesis of Taxol Side-Chain Synthon. Ann NY Acad Sci 750 166... 

Waite, D. C. and Mason, C. P. A Scalable Synthesis Of The Thromboxane Receptor Antagonist3- 3-[2-(4-Chlorobenzenesulfonamido)Ethyl]-5-(4Fluorobenzyl)Phenyl Propionic Acid via a Regioselective Heck Cross-Coupling Strategy. Org Process Res Dev 2,116-120(1998). 

Hydrolysis methods for mono[ C]nitriles and the spectrum of chemical transformations of the resulting [l- C]carboxylic acids differ little from those for their unlabeled counterparts, so that the synthesis of [l- C]tetralones 42 and [l- " C]indanones 46 from w-arylalkyl [ C]nitriles will suffice as examples (Figure 7.11). Acid-catalyzed hydrolysis of 4-phenylbutyro[ C]nitrile followed by polyphosphoric acid-mediated cyclization of the resulting phenyl[l- C]butanoic acid converted it into 42 in 89% radiochemical yield. Sequential bromination and oxime formation provided the a-bromooxime 43, which upon treatment with polyphosphoric acid underwent a Beckman rearrangement to provide the ring-expanded tetrahydro-2H-l-[2- C]benzazepine-2-one derivative 44- This was a key intermediate for the preparation of a series of labeled ACE inhibitors" . The acid-catalyzed cyclization of a mixture of 3-(2-hydroxyphenyl[l- " C]propionic acid and its ethyl ester, prepared by treatment of the propio[ " C]nitrile with ethanolic HCI proved to be a two-step sequence. In the first step, 2- [2- " C ]chromanone I4SI was formed and had to be submitted to... 

An experiment which is difficult to classify, but which probably belongs to this category, is the synthesis of optically active 8-phenyl-/8-hydroxy-propionic acid XII reported by Abbott, Christie, and McKenzie (1) ... 

Figure 11 Synthesis of taxol side chain synthon Stereoselective microbial reduction of 2-keto-3-(iV-benzoylamino)-3-phenyl propionic acid, ethyl ester 40.

AO containing various phenolic moieties were prepared by transesterification in the presence of tetraalkyl titanates. Randomly distributed -active moieties are characteristic of 140 (only the hard polyester segment is given) prepared from dimethyl terephthalate, 1,4-butanediol, poly(tetramethylene oxide)diol and dimethyl 5-(3,5-di-tm-butyl-4-hydroxybenzenepropaneamido)isophthalate [181]. The mentioned polymeric AO was used for stabilization of polyether-polyester elastomers. A partial attachement of tetrakis[methylene 3(3,5-di-tert-butyl-4-hydroxy-phenyl)propionate]methane (3) via transesterification reaction was expected in the synthesis of another polyether-polyester elastomer by [182]. A reversible redox polyester was formed from 2,5-bis(2-hydroxyethyl)hydroquinone and dichlorides of aliphatic dicarboxylic acids [137],... 

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