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

HRID 2297050Notes

Reaction equation

HRID 2297050 reaction equation
[C:1]1([N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[C:8]2[C:16]([NH:18][C@H:19]([C:23]([NH:25][CH:26]([C:35](=[O:38])[CH2:36][F:37])[CH2:27][C:28]([O:30]C(C)(C)C)=[O:29])=[O:24])[CH:20]([CH3:22])[CH3:21])=[O:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(C(F)(F)F)=O>C1(OC)C=CC=CC=1.C(Cl)Cl>[C:1]1([N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[C:8]2[C:16]([NH:18][C@H:19]([C:23]([NH:25][CH:26]([C:35](=[O:38])[CH2:36][F:37])[CH2:27][C:28]([OH:30])=[O:29])=[O:24])[CH:20]([CH3:21])[CH3:22])=[O:17])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86584008N-[(1-Phenylindole-2-Carbonyl)Valinyl]-3-Amino-4-Oxo-5-Fluoropentanoic Acid, t-Butyl Ester

Product 1

HCID 22942392N-[(1-Phenylindole-2-Carbonyl)Valinyl]-3-Amino-4-Oxo-5-Fluoropentanoic AcidYield 72.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

A solution of N-[(1-phenylindole-2-carbonyl)valinyl]-3-amino-4-oxo-5-fluoropentanoic acid, t-butyl ester (154 mg) in anisole (0.2 mL) and methylene chloride (2 mL) was treat d with TFA (1 mL), and the resultant reaction mixture was stirred for one hour under nitrogen atmosphere at room temperature. The reaction mixture was concentrated and chased with methylene chloride, then triturated with ether to yield the title product as white powder (100 mg). TLC (methylene chloride/methanol/acetic acid, 20:1:1): Rf=0.38, MS for C25H26FN3O5: MH+=468; (M−H)+=466.

Workup

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

Sources & evidence

ORD record
ord-25d58355060f460f94b56480706a7f9a
Source dataset
uspto-grants-2002_12
Patent number
US06489353B2

Reaction notes

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