D-Phenylalanine → HCID 178448095, compound

HRID 245348Notes

Reaction equation

HRID 245348 reaction equation
[CH:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([C:10](Cl)=[O:11])[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[NH2:13][C@@H:14]([C:22]([OH:24])=[O:23])[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O>[CH3:2][CH:1]([CH3:3])[C@@H:4]1[CH2:9][CH2:8][C@@H:7]([C:10]([NH:13][C@H:14]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:22]([OH:24])=[O:23])=[O:11])[CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 71567D-PhenylalanineHCID 178448093HCID 178448093, compound

Product 1

HCID 178448095HCID 178448095, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

EP1334963A discloses a method for producing nateglinide crystals from a reaction mixture containing nateglinide. The nateglinide is obtained by reacting trans-4-isopropylcyclohexane carboxylic acid chloride with D-phenylalanine in a mixed solvent of a ketone and water in the presence of an alkali, followed by neutralisation with an acid. Specific adjustment of the temperature of the mixture and the concentration of ketone solvent results in precipitation of nateglinide crystals. The ketone solvent(s) in the reaction is usually essential to proceed the reaction. However, a large quantity of acetone in the reaction causes high proportion of by-product.

Sources & evidence

ORD record
ord-e4967e728f3f48cfb34803717d20403b
Source dataset
uspto-grants-2014_02
Patent number
US08658821B2

Reaction notes

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