Trifluoroacetic acid → 204919-14-2

HRID 362490Notes

Reaction equation

HRID 362490 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH3:11])=[C:3]1[C:12]([NH:14][C@H:15]([C:19]([NH:21][CH:22]([C:31](=[O:34])[CH2:32][F:33])[CH2:23][C:24]([O:26]C(C)(C)C)=[O:25])=[O:20])[CH:16]([CH3:18])[CH3:17])=[O:13].FC(F)(F)C(O)=O>C1(OC)C=CC=CC=1.C(Cl)Cl>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH3:11])=[C:3]1[C:12]([NH:14][C@H:15]([C:19]([NH:21][CH:22]([C:31](=[O:34])[CH2:32][F:33])[CH2:23][C:24]([OH:26])=[O:25])=[O:20])[CH:16]([CH3:17])[CH3:18])=[O:13]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86584477HCID 86584477, compound

Product 1

HCID 9802179204919-14-2Yield 48.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

A solution of N-[(1,3-dimethylindole-2-carbonyl)valinyl]-3-amino-4-oxo-5-fluoropentanoic acid, t-butyl ester (40 mg) in anisole (0.2 mL) and methylene chloride (2 mL) was treated with trifluoroacetic acid (1 mL), and the resultant reaction mixture was stirred for 30 minutes under a nitrogen atmosphere at room temperature. The reaction mixture was concentrated and chased with methylene chloride to give a solid. The solid was triturated with ether to yield the title product as a brown powder (17 mg). TLC: (methylene chloride/methanol/acetic acid, 20:1:1): Rf =0.40. MS (EI) for C21H26FN3O5 : MH+ =420; MH- =418.

Workup

  1. customthe resultant reaction mixture
  2. concentrationThe reaction mixture was concentrated
  3. customto give a solid
  4. customThe solid was triturated with ether

Sources & evidence

ORD record
ord-d47865f891454c02a3f55fe7c4f9c0c8
Source dataset
uspto-grants-1999_02
Patent number
US05869519

Reaction notes

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