(2S)-2-[[2-(3,5-difluorophenyl)acetyl]amino]propanoic acid → Methyl N-[N-(3,5-Difluorophenylacetyl)-L-alaninyl]-(S)-2-amino3-(2-naphthyl)propionate

HRID 983272Notes

Reaction equation

HRID 983272 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.Cl.[NH2:19][C@@H:20]([CH2:25][C:26]1[CH:35]=[CH:34][C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=1)[C:21]([O:23][CH3:24])=[O:22]>CO.C(Cl)Cl>[F:8][C:6]1[CH:5]=[C:4]([CH2:9][C:10]([NH:12][C@H:13]([C:15]([NH:19][C@@H:20]([CH2:25][C:26]2[CH:35]=[CH:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH:27]=2)[C:21]([O:23][CH3:24])=[O:22])=[O:17])[CH3:14])=[O:11])[CH:3]=[C:2]([F:1])[CH:7]=1

Participants

4

Reactant 2

HCID 12135350(2S)-2-[[2-(3,5-difluorophenyl)acetyl]amino]propanoic acidHCID 56777259methyl (2S)-2-amino-3-(naphthalen-2-yl)propanoate hydrochloride

Product 1

HCID 9955580Methyl N-[N-(3,5-Difluorophenylacetyl)-L-alaninyl]-(S)-2-amino3-(2-naphthyl)propionate

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Following General Procedure B and using N-(3,5-difluorophenylacetyl)-L-alanine (from Example B2 above) and methyl (S)-2-amino-3-(2-naphthyl)propionate hydrochloride (Bachem), the title compound was prepared as a solid (mp=166° C.). The reaction was monitored by tlc (Rf=0.55 in 5% MeOH/methylene chloride) and the product was purified by preparative tlc using 5% MeOH/methylene chloride as the eluent.

Workup

  1. customthe product was purified by preparative tlc

Sources & evidence

ORD record
ord-d0e32bc7c6b441ad98f3e1ca5a8f6d0e
Source dataset
uspto-grants-2005_03
Patent number
US06861558B2

Reaction notes

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