Cyclopentylacetic acid → 2-(2-Cyclopentyl-acetylamino)-3-(3-hydroxy-phenyl)-propionic acid methyl ester

HRID 1272686Notes

Reaction equation

HRID 1272686 reaction equation
[CH3:1][O:2][C:3](=[O:14])[CH:4]([NH2:13])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([OH:12])[CH:7]=1.[CH:15]1([CH2:20][C:21](O)=[O:22])[CH2:19][CH2:18][CH2:17][CH2:16]1>>[CH3:1][O:2][C:3](=[O:14])[CH:4]([NH:13][C:21](=[O:22])[CH2:20][CH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([OH:12])[CH:7]=1

Participants

3

Reactant 2

HCID 71606Cyclopentylacetic acidHCID 22386100Methyl 2-amino-3-(3-hydroxyphenyl)propanoate

Product 1

HCID 688714192-(2-Cyclopentyl-acetylamino)-3-(3-hydroxy-phenyl)-propionic acid methyl esterYield 54.9%

Procedure

12.5 g (54.3 mmol) of 2-amino-3-(3-hydroxy-phenyl)-propionic acid methyl ester was reacted with cyclopentyl acetic acid (6.97 g, 54.3 mmol) as described in general procedure A. The compound was purified using gradient elution with ethyl acetate in hexanes to yield 9.1 g of 2-(2-cyclopentyl-acetylamino)-3-(3-hydroxy-phenyl)-propionic acid methyl ester.

Workup

  1. customThe compound was purified
  2. washelution with ethyl acetate in hexanes

Sources & evidence

ORD record
ord-494cabc8625d40c5afb7d8e765fef5a6
Source dataset
uspto-grants-2007_04
Patent number
US07208601B2

Reaction notes

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