Methyl tryptophanate hydrochloride → N-(N-(3,5-Difluorophenylacetyl)-L-alaninyl]-L-tryptophan Methyl Ester

HRID 322743Notes

Reaction equation

HRID 322743 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.[CH3:19][O:20][C:21](=[O:34])[C@H:22]([CH2:24][C:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[NH:27][CH:26]=1)[NH2:23]>CO.C(Cl)(Cl)Cl>[CH3:19][O:20][C:21](=[O:34])[C@H:22]([CH2:24][C:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[NH:27][CH:26]=1)[NH:23][C:15](=[O:17])[C@H:13]([CH3:14])[NH:12][C:10](=[O:11])[CH2:9][C:4]1[CH:5]=[C:6]([F:8])[CH:7]=[C:2]([F:1])[CH:3]=1

Participants

4

Reactant 2

HCID 2734891Methyl tryptophanate hydrochlorideHCID 12135350(2S)-2-[[2-(3,5-difluorophenyl)acetyl]amino]propanoic acid

Product 1

HCID 22894900N-(N-(3,5-Difluorophenylacetyl)-L-alaninyl]-L-tryptophan Methyl Ester

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

Following General Procedure C and using N-(3,5-difluorophenylacetyl)-L-alanine (from Example B2 above) and L-tryptophan methyl ester hydrochloride (Sigma), the title compound was prepared as a solid (mp=191-193° C.). The reaction was monitored by tlc (Rf=0.4 in 10% MeOH/CHCl3) and the product was purified by silica gel chromatography using 5% MeOH/CHCl3 as the eluent, followed by recrystallization from 1-chlorobutane/acetonitrile.

Workup

  1. customthe product was purified by silica gel chromatography
  2. customfollowed by recrystallization from 1-chlorobutane/acetonitrile

Sources & evidence

ORD record
ord-dd5fefba19f44cfa9be8674d8c2cb7be
Source dataset
uspto-grants-2001_04
Patent number
US06211235B1

Reaction notes

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