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

HRID 634956Notes

Reaction equation

C([O:5][C:6](=[O:50])[CH2:7][CH:8]([NH:23][C:24](=[O:49])[C@H:25]([CH:46]([CH3:48])[CH3:47])[NH:26][C:27]([C:29]1[N:30]([CH2:38][C:39]([O:41]C(C)(C)C)=[O:40])[C:31]2[C:36]([CH:37]=1)=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:28])[C:9](=[O:22])[CH2:10][O:11][C:12]1[C:17]([F:18])=[C:16]([F:19])[CH:15]=[C:14]([F:20])[C:13]=1[F:21])(C)(C)C.C(O)(C(F)(F)F)=O>>[C:39]([CH2:38][N:30]1[C:31]2[C:36](=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:37]=[C:29]1[C:27]([NH:26][C@H:25]([C:24]([NH:23][CH:8]([C:9](=[O:22])[CH2:10][O:11][C:12]1[C:13]([F:21])=[C:14]([F:20])[CH:15]=[C:16]([F:19])[C:17]=1[F:18])[CH2:7][C:6]([OH:50])=[O:5])=[O:49])[CH:46]([CH3:47])[CH3:48])=[O:28])([OH:41])=[O:40]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 86756376N-{[1-(tert-butyl)oxycarbonylmethyl-indole-2-cabonyl]valinyl}-3-amino-4-oxo-5-(2,3,5,6-tetrafluorophenyloxy)-pentanoic Acid, tert-butyl Ester

Product 1

HCID 20639704N-{[1-(carboxymethyl)-indole-2-cabonyl]valinyl}-3-amino-4-oxo-5-(2,3,5,6-tetrafluorophenyloxy)-pentanoic acid

Procedure

Treatment of N-{[1-(tert-butyl)oxycarbonylmethyl-indole-2-carbonyl]valinyl}-3-amino-4-oxo-5-(2,3,5,6-tetrafluorophenyloxy)-pentanoic acid tert-butyl ester with TFA as described in Example 80 gave the titled product as a white powder. MS C27H25F4N3O8, [M+H]+ =596, [M−H]− =594.

Sources & evidence

ORD record: ord-6226e1843f9d4a88a95c087b18d452a1
Source dataset: uspto-grants-2001_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06184244B2

Reaction notes

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