Trifluoroacetic acid → N-[2-chloro-4-carboxybenzoyl]-4-(2-methoxyphenyl)-L-phenylalanine methyl ester

HRID 24669Notes

Reaction equation

HRID 24669 reaction equation
[CH3:1][O:2][C:3](=[O:37])[C@H:4]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[O:35][CH3:36])=[CH:25][CH:24]=1)[NH:5][C:6](=[O:21])[C:7]1[CH:12]=[CH:11][C:10]([C:13]([O:15]C(C)(C)C)=[O:14])=[CH:9][C:8]=1[Cl:20].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:37])[C@H:4]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[O:35][CH3:36])=[CH:25][CH:24]=1)[NH:5][C:6](=[O:21])[C:7]1[CH:12]=[CH:11][C:10]([C:13]([OH:15])=[O:14])=[CH:9][C:8]=1[Cl:20]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 53704971N-[2-chloro-4-(tert-butoxycarbonyl)benzoyl]-4-(2-methoxyphenyl)-L-phenylalanine methyl ester

Product 1

HCID 53769879N-[2-chloro-4-carboxybenzoyl]-4-(2-methoxyphenyl)-L-phenylalanine methyl esterYield 115.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-[2-Chloro-4-(tert-butoxycarbonyl)benzoyl]-4-(2-methoxyphenyl)-L-phenylalanine methyl ester (305 mg) was dissolved in anhydrous CH2Cl2 (2 mL) under N2 and TFA (2 mL) was added. The mixture was stirred at room temperature for 2 h to give N-[2-chloro-4-carboxybenzoyl]-4-(2-methoxyphenyl)-L-phenylalanine methyl ester (315 mg).

Sources & evidence

ORD record
ord-cf122efb8bae4248a7afa868c581db98
Source dataset
uspto-grants-2005_02
Patent number
US06855843B2

Reaction notes

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