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

HRID 397456Notes

Reaction equation

HRID 397456 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 treated with TFA (1 mL), and the resultant reaction mixture was stirred for one hour under a 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 a white powder (100 mg). TLC: (methylene chloride/methanol/acetic acid, 20:1:1): Rf=0.38, MS (EI) for C25H26FN5O5: 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-ab73eb1ac06b4cc292c1797b13408499
Source dataset
uspto-grants-2003_08
Patent number
US06610683B2

Reaction notes

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