(S)-Methyl 2-amino-3-(thiophen-2-yl)propanoate → Methyl N-(N-(3,5Difluorophenylacetyl)-L-alaninyl]-(S)-2-amino3-(2-thienyl)propionate

HRID 2180782Notes

Reaction equation

HRID 2180782 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][C@@H:19]([CH2:24][C:25]1[S:26][CH:27]=[CH:28][CH:29]=1)[C:20]([O:22][CH3:23])=[O:21]>CCOC(C)=O>[F:8][C:6]1[CH:5]=[C:4]([CH2:9][C:10]([NH:12][C@H:13]([C:15]([NH:18][C@@H:19]([CH2:24][C:25]2[S:26][CH:27]=[CH:28][CH:29]=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

4

Reactant 2

HCID 10899351(S)-Methyl 2-amino-3-(thiophen-2-yl)propanoateHCID 12135350(2S)-2-[[2-(3,5-difluorophenyl)acetyl]amino]propanoic acid

Product 1

HCID 10112224Methyl N-(N-(3,5Difluorophenylacetyl)-L-alaninyl]-(S)-2-amino3-(2-thienyl)propionate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Following General Procedure B and using N-(3,5-difluorophenylacetyl)-L-alanine (from Example B2 above) and methyl (S)-2-amino-3-(2-thienyl)-propionate (Bachem), the title compound was prepared as a solid (mp=145-147° C.). The reaction was monitored by tlc (Rf=0.9 in 100% EtOAc) and the product was purified by preparative tlc using EtOAc as the eluent.

Workup

  1. customthe product was purified by preparative tlc

Sources & evidence

ORD record
ord-b1daf60b96d54037a0d944eccb38d03e
Source dataset
uspto-grants-2005_05
Patent number
US06888022B2

Reaction notes

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