Trifluoroacetic acid → 4-[(2-chloro-5-cyanophenylcarbonyl)amino]-L-phenylalanine methyl ester TFA salt

HRID 393471Notes

Reaction equation

HRID 393471 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.[F:33][C:34]([F:39])([F:38])[C:35]([OH:37])=[O:36]>ClCCl>[OH:37][C:35]([C:34]([F:39])([F:38])[F:33])=[O:36].[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 1317235094-[(2-chloro-5-cyanophenylcarbonyl)amino]-L-phenylalanine methyl ester TFA saltYield 100%

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 h at room temperature at which time TLC analysis of the mixture indicated the absence of starting material. Then, the solvent was removed under vacuum and the residue was azeotroped with toluene (2×10 mL) and dried under high vacuum to afford 0.43 g (100%) of a yellow solid. HR MS (C18H16ClN3O3): Obs mass, 358.0963. Calcd mass, 358.0959 (M+H).

Workup

  1. customThen, the solvent was removed under vacuum
  2. customthe residue was azeotroped with toluene (2×10 mL)
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-540de501b2e645af933d9150402f448e
Source dataset
uspto-grants-2004_10
Patent number
US06806365B2

Reaction notes

Loading…