Trifluoroacetic acid → N-[(3-Chloro-5-Fluoro-1-Methylindole-2-Carbonyl)Valinyl]-3-Amino-4-Oxo-5-Fluoropentanoic Acid

HRID 397454Notes

Reaction equation

HRID 397454 reaction equation
[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([F:11])[CH:9]=2)[N:4]([CH3:12])[C:3]=1[C:13]([NH:15][C@H:16]([C:20]([NH:22][CH:23]([C:32](=[O:35])[CH2:33][F:34])[CH2:24][C:25]([O:27]C(C)(C)C)=[O:26])=[O:21])[CH:17]([CH3:19])[CH3:18])=[O:14].C(O)(C(F)(F)F)=O>C1(OC)C=CC=CC=1.C(Cl)Cl>[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([F:11])[CH:9]=2)[N:4]([CH3:12])[C:3]=1[C:13]([NH:15][C@H:16]([C:20]([NH:22][CH:23]([C:32](=[O:35])[CH2:33][F:34])[CH2:24][C:25]([OH:27])=[O:26])=[O:21])[CH:17]([CH3:18])[CH3:19])=[O:14]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86584006N-[(3-chloro-5-fluoro-1-methylindole-2-carbonyl) valinyl]-3-amino-4-oxo-5-fluoropentanoic acid, t-butyl ester

Product 1

HCID 22942394N-[(3-Chloro-5-Fluoro-1-Methylindole-2-Carbonyl)Valinyl]-3-Amino-4-Oxo-5-Fluoropentanoic AcidYield 82.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

A solution of N-[(3-chloro-5-fluoro-1-methylindole-2-carbonyl)Valinyl]-3-amino-4-oxo-5-fluoropentanoic acid, t-butyl ester (682 mg) in anisole (1 mL) and methylene chloride (10 mL) was treated with TFA (5 mL), and the resultant reaction mixture was stirred for 45 minutes under a nitrogen atmosphere at room temperature. The reaction mixture was concentrated and chased with methylene chloride, then triturated with ether to afford the title product as a white powder (500 mg). MS (EI) for C20H22CIF2N3O5: MH+=458/460; (M−H)−=456/458.

Workup

  1. customthe resultant reaction mixture
  2. concentrationThe reaction mixture was concentrated
  3. customtriturated with ether

Sources & evidence

ORD record
ord-d9f171129456488c849635e4859ab136
Source dataset
uspto-grants-2003_08
Patent number
US06610683B2

Reaction notes

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