Trifluoroacetic acid → n-[(1,3-Dimethylindole-2-carbonyl)valinyl]-3-amino-4-oxo-5-(2'6'-dichlorobenzyloxy)pentanoic acid

HRID 397449Notes

Reaction equation

HRID 397449 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:43])[CH2:32][O:33][CH2:34][C:35]1[C:40]([Cl:41])=[CH:39][CH:38]=[CH:37][C:36]=1[Cl:42])[CH2:23][C:24]([O:26]C(C)(C)C)=[O:25])=[O:20])[CH:16]([CH3:18])[CH3:17])=[O:13].C(O)(C(F)(F)F)=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:43])[CH2:32][O:33][CH2:34][C:35]1[C:40]([Cl:41])=[CH:39][CH:38]=[CH:37][C:36]=1[Cl:42])[CH2:23][C:24]([OH:26])=[O:25])=[O:20])[CH:16]([CH3:18])[CH3:17])=[O:13]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86584003N-[(1,3-dimethylindole-2-carbonyl)valinyl]-3-amino-4-oxo-5-(2'6'-dichlorobenzyloxy)pentanoic Acid, T-Butyl Ester

Product 1

HCID 22942386n-[(1,3-Dimethylindole-2-carbonyl)valinyl]-3-amino-4-oxo-5-(2'6'-dichlorobenzyloxy)pentanoic acidYield 76.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

A solution of N-[(1,3-Dimethylindole-2-carbonyl)valinyl]-3-amino-4-oxo-5-(2′,6′-dichloro-benzyloxy)pentanoic acid, t-butyl ester (49 mg) in anisole (0.2 mL) and methylene chloride (2 mL) was treated with TFA (1 ml) and stirred for 30 minutes under a nitrogen atmosphere at room temperature. The resultant solution was concentrated and chased with methylene chloride to give a white solid as the crude product. The crude product was triturated with ether to yield the title product as a white powder (34 mg). MS(EI) for C28H31Cl2N3O6; MH+=576/578; (MH)−=574/576.

Workup

  1. concentrationThe resultant solution was concentrated
  2. customto give a white solid as the crude product
  3. customThe crude product was triturated with ether

Sources & evidence

ORD record
ord-af5953de05b544e38884f9a406e6328d
Source dataset
uspto-grants-2003_08
Patent number
US06610683B2

Reaction notes

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