Methyl -2-hydroxy-4-phenyl butyrate

The Step 7 product (160 mg) dissolved in 5 ml CH2C12 was treated with 67 pi methyl-morpholine, isopropyl (2/LS, 3.V)-3-amino-2-hydroxy-4-phenyl butyrate (144 mg) and 1-hydroxybenzotriazole (103 mg), then cooled, and l-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (116 mg) added. The mixture was stirred overnight and was then extracted using EtOAc. The extract was washed successively with 0.1 M NaOH solution, brine, 0.1M HC1, brine, dried, and then concentrated. The residue was purified by chromatography with silica gel and 259 mg product isolated. 

The first technical application of a cinchona-modified Pt catalyst was reported by Ciba-Geigy in 1986 for the synthesis of methyl (R)-2-hydroxy-4-phenyl butyrate (R)-HPB ester), an intermediate for the ACE inhibitor benazepril depicted in Figure 2.10 [44a],... 

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It is interesting to note that in fermented products the same alcohols always form, even if different sources of nitrogen, but not singular aminoacids, are available. Ketoacids can also be directly reduced to hydroxyacids such as lactic, 2-hydroxy-3-methyl butyric, 2-hydroxy-3-methyl pentanoic, 2-hydroxy-4-methyl pentanoic, 2-hydroxy-3-phenyl propionic and 2-hydroxy glutaric acids. The corresponding ethyl esters can dramatically influence the wine aroma. 

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