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

HRID 1984858Notes

Reaction equation

HRID 1984858 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 10% to 100% 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 10% to 100% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-0e04959f4fa84717a0fc12d0baa3e2cf
Source dataset
uspto-grants-2009_06
Patent number
US07544699B2

Reaction notes

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