Ketoprofen → rac Ketoprofen AMide

HRID 1534324Notes

Reaction equation

CC([NH2:9])C1C=CC=CC=1.[OH:10][C:11]([CH:13]([C:15]1[CH:28]=[CH:27][CH:26]=[C:17]([C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:19])[CH:16]=1)[CH3:14])=O>>[CH3:14][CH:13]([C:11]([NH2:9])=[O:10])[C:15]1[CH:16]=[C:17]([C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:19])[CH:26]=[CH:27][CH:28]=1

Participants

Reactant 2

HCID 3825Ketoprofen2×

HCID 74081-Phenethylamine

Product 1

HCID 3042314rac Ketoprofen AMide

Procedure

The basic phase is acidified and is then extracted with chloroform. After forming the R (+) α-methylbenzylamine derivative of ketoprofen, analysis of the mixture of the two diastereoisomers by high performance liquid chromatography shows that the enantiomeric excess of S (+) ketoprofen is 93%.

Workup

extractionis then extracted with chloroform
customAfter forming

Sources & evidence

ORD record: ord-94d29c0d80394f228f106d320bfd2269
Source dataset: uspto-grants-1992_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05089405

Reaction notes

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