Trifluoroacetic acid → N-[(1-methyl-indole-2-cabonyl)valinyl]-3-amino-4-oxo-5-(2,3,5,6-tetrafluorophenyloxy)-pentanoic acid

HRID 634951Notes

Reaction equation

[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:11]([NH:13][C@H:14]([C:18]([NH:20][CH:21]([C:30](=[O:43])[CH2:31][O:32][C:33]1[C:38]([F:39])=[C:37]([F:40])[CH:36]=[C:35]([F:41])[C:34]=1[F:42])[CH2:22][C:23]([O:25]C(C)(C)C)=[O:24])=[O:19])[CH:15]([CH3:17])[CH3:16])=[O:12].C(O)(C(F)(F)F)=O>>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:11]([NH:13][C@H:14]([C:18]([NH:20][CH:21]([C:30](=[O:43])[CH2:31][O:32][C:33]1[C:38]([F:39])=[C:37]([F:40])[CH:36]=[C:35]([F:41])[C:34]=1[F:42])[CH2:22][C:23]([OH:25])=[O:24])=[O:19])[CH:15]([CH3:17])[CH3:16])=[O:12]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 86756372N-[(1-methyl-indole-2-cabonyl)valinyl]-3-amino-4-oxo-5-(2,3,5,6-tetrafluorophenyloxy)-pentanoic Acid, tert-butyl Ester

Product 1

HCID 20639716N-[(1-methyl-indole-2-cabonyl)valinyl]-3-amino-4-oxo-5-(2,3,5,6-tetrafluorophenyloxy)-pentanoic acidYield 95%

Procedure

Treatment of N-[(1-methyl-indole-2-carbonyl)valinyl]-3-amino-4-oxo-5-(2,3,5,6-tetrafluorophenyloxy)-pentanoic acid, tert-butyl ester (120 mg, 0.20 mmol) with TFA as described in Example 80 gave the titled product (104 mg, 95%) as a white powder. MS C26H25F4N3O6, [M+Na]+ =574, [M−H]− =550.

Sources & evidence

ORD record: ord-4516378114454d07afc8622bd065eb6e
Source dataset: uspto-grants-2001_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06184244B2

Reaction notes

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