D-Phenylalanine → HCID 178448095, compound

HRID 1746339Notes

Reaction equation

HRID 1746339 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].C([C@H]1CC[C@H](C(O)=O)CC1)(C)C.[NH2:25][C@@H:26]([C:34]([OH:36])=[O:35])[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>O.CC(C)=O>[CH3:2][CH:1]([CH3:3])[C@@H:4]1[CH2:9][CH2:8][C@@H:7]([C:10]([NH:25][C@H:26]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:34]([OH:36])=[O:35])=[O:11])[CH2:6][CH2:5]1

Participants

6

Reactant 3

HCID 71567D-PhenylalanineHCID 178448093HCID 178448093, compoundHCID 178448099HCID 178448099, compound

Product 1

HCID 178448095HCID 178448095, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

U.S. Pat. No. 7,208,622 describes a process in which trans-4-isopropylcyclohexane carbonyl chloride (i.e. a derivative of trans-4-isopropylcyclohexane carboxylic acid) is reacted with D-phenylalanine in the presence of a caustic solution followed by acidification in a mixture of water and acetone and crystallization at 58-72° C. which results in Form H of nateglinide.

Sources & evidence

ORD record
ord-f2bbb2fb931e458eae0d7b04d5ff9dc5
Source dataset
uspto-grants-2015_10
Patent number
US09150499B2

Reaction notes

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