(2S)-2-[[2-(3,5-difluorophenyl)acetyl]amino]propanoic acid → Methyl N-[N-(3,5-Difluorophenylacetyl)-L-alaninyl]-2-amino-2-(2-thienyl)acetate

HRID 636226Notes

Reaction equation

HRID 636226 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:24]1[S:25][CH:26]=[CH:27][CH:28]=1)[C:20]([O:22][CH3:23])=[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:24]2[S:25][CH:26]=[CH:27][CH:28]=2)[C:20]([O:22][CH3:23])=[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 13848532Methyl 2-amino-2-(thiophen-2-yl)acetate

Product 1

HCID 22894858Methyl N-[N-(3,5-Difluorophenylacetyl)-L-alaninyl]-2-amino-2-(2-thienyl)acetate

Procedure

Following General Procedure C and using N-(3,5-difluorophenylacetyl)-L-alanine (from Example B2 above) and methyl 2-amino-2-(2-thienyl)acetate (prepared from L-α-2-thienylglycine (Sigma) using General Procedure G), the title compound was prepared as a solid (mp=161-162° C.). The product was purified by preparative LC 2000 chromatography using 1:4 EtOAc/hexanes.

Workup

  1. customThe product was purified by preparative LC 2000 chromatography

Sources & evidence

ORD record
ord-331161f6ee8d4198ac8d5f42cd836c1f
Source dataset
uspto-grants-2001_02
Patent number
US06191166B1

Reaction notes

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