(2S)-2-[[2-(3,5-difluorophenyl)acetyl]amino]propanoic acid → HCID 22894868, compound

HRID 1016955Notes

Reaction equation

HRID 1016955 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([NH:12][C@H:13]([C:15]([OH:17])=O)[CH3:14])=[O:11])[CH:5]=[C:6]([F:8])[CH:7]=1.[NH2:18][CH:19]([C:25]1[CH:26]=[CH:27][C:28]2[S:32][CH:31]=[CH:30][C:29]=2[CH:33]=1)[C:20]([O:22][CH2:23][CH3:24])=[O:21]>>[F:8][C:6]1[CH:5]=[C:4]([CH2:9][C:10]([NH:12][C@H:13]([C:15]([NH:18][CH:19]([C:25]2[CH:26]=[CH:27][C:28]3[S:32][CH:31]=[CH:30][C:29]=3[CH:33]=2)[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[O:17])[CH3:14])=[O:11])[CH:3]=[C:2]([F:1])[CH:7]=1

Participants

3

Reactant 2

HCID 12135350(2S)-2-[[2-(3,5-difluorophenyl)acetyl]amino]propanoic acidHCID 22492192HCID 22492192, compound

Product 1

HCID 22894868HCID 22894868, compound

Procedure

Following General Procedure C and using N-(3,5-difluorophenylacetyl)-L-alanine (from Example B2 above) and ethyl 2-amino-2-(benzothiophen-5-yl)acetate (prepared as described in S. Kukolja et al., J Med. Chem., 1985, 28, 1896-1903), the title compound was prepared as a solid (mp=126.5-127.5° C.). The product was purified by preparative LC 2000 chromatography using 1:1 hexanes/EtOAc as the eluent.

Workup

  1. customThe product was purified by preparative LC 2000 chromatography

Sources & evidence

ORD record
ord-161b2c3ed61149b3bc96d533d40f5634
Source dataset
uspto-grants-2002_11
Patent number
US06476263B1

Reaction notes

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