Trifluoroacetic acid → 4-[[(2-chloro-5-cyanophenyl)carbonyl]amino]-L-phenylalanine methyl ester

HRID 1976974Notes

Reaction equation

HRID 1976974 reaction equation
[CH3:1][O:2][C:3](=[O:32])[C@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21]([C:23]2[CH:28]=[C:27]([C:29]#[N:30])[CH:26]=[CH:25][C:24]=2[Cl:31])=[O:22])=[CH:16][CH:15]=1)[NH:5]C(OC(C)(C)C)=O.FC(F)(F)C(O)=O>ClCCl>[CH3:1][O:2][C:3](=[O:32])[C@H:4]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([NH:20][C:21]([C:23]2[CH:28]=[C:27]([C:29]#[N:30])[CH:26]=[CH:25][C:24]=2[Cl:31])=[O:22])=[CH:18][CH:19]=1)[NH2:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 539100724-[(2-chloro-5-cyanophenylcarbonyl)amino]-N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanine methyl ester

Product 1

HCID 541933924-[[(2-chloro-5-cyanophenyl)carbonyl]amino]-L-phenylalanine methyl esterYield 100.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[(2-chloro-5-cyanophenylcarbonyl)amino]-N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanine methyl ester (1.2 mmol, 0.55 g) in dichloromethane (12 mL) was added trifluoroacetic acid (3 mL) at room temperature. The reaction mixture was stirred for 15 hr at room temperature at which time TLC analysis of the mixture indicated the absence of starting material. The solvent was removed under vacuum and the residue was azeotrophed with toluene (2×10 mL) and dried under high vacuum to afford 0.43 g (100%) of an yellow solid. HR MS: Obs. mass, 358.0963. Calcd. mass, 358.0959 (M+H).

Workup

  1. customThe solvent was removed under vacuum
  2. customdried under high vacuum

Sources & evidence

ORD record
ord-f0d41b6589934394b4a2b6e72965d30c
Source dataset
uspto-grants-2001_05
Patent number
US06229011B1

Reaction notes

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