Tyrosine Methyl Ester → (2S)-{[7-(4-tert-Butyl-phenoxy)-isoquinoline-3-carbonyl]-amino}-3-(4-hydroxy-phenyl)-propionic acid methyl ester

HRID 1984829Notes

Reaction equation

HRID 1984829 reaction equation
[C:1]([C:5]1[CH:24]=[CH:23][C:8]([O:9][C:10]2[CH:19]=[C:18]3[C:13]([CH:14]=[C:15]([C:20](O)=[O:21])[N:16]=[CH:17]3)=[CH:12][CH:11]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:25][O:26][C:27](=[O:38])[C@@H:28]([NH2:37])[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=1>>[CH3:25][O:26][C:27](=[O:38])[C@@H:28]([NH:37][C:20]([C:15]1[N:16]=[CH:17][C:18]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[C:10]([O:9][C:8]1[CH:23]=[CH:24][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][CH:7]=1)[CH:19]=2)=[O:21])[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=1

Participants

3

Reactant 2

HCID 70652Tyrosine Methyl EsterHCID 184576667-(4-tert-Butylphenoxy)-isoquinoline-3-carboxylic acid

Product 1

HCID 57717726(2S)-{[7-(4-tert-Butyl-phenoxy)-isoquinoline-3-carbonyl]-amino}-3-(4-hydroxy-phenyl)-propionic acid methyl esterYield 75.2%

Procedure

500 mg (1.6 mmol) of 7-(4-tert-Butylphenoxy)-isoquinoline-3-carboxylic acid was reacted with 430 mg (1.8 mmol) of (2S)-amino-3-(4-hydroxy-phenyl)-propionic acid methyl ester as described in general procedure A. The crude product was purified by flash column chromatography on silica gel using 3:2 hexane/ethyl acetate as eluent, to afford 600 mg of the title compound as a white solid.

Workup

  1. customThe crude product was purified by flash column chromatography on silica gel using 3:2 hexane/ethyl acetate as eluent

Sources & evidence

ORD record
ord-63bc85b6f11441f8869af62e97cac44c
Source dataset
uspto-grants-2009_06
Patent number
US07544699B2

Reaction notes

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