Trifluoroacetic acid → N-[(1-methyl-3-isobutyl-indole-2-cabonyl)valinyl]-3-amino-4-oxo-5-(4-fluorophenyloxy)-pentanoic Acid

HRID 2297055Notes

Reaction equation

[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][CH:12]([CH3:14])[CH3:13])=[C:3]1[C:15]([NH:17][C@H:18]([C:22]([NH:24][CH:25]([C:34](=[O:44])[CH2:35][O:36][C:37]1[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=1)[CH2:26][C:27]([O:29]C(C)(C)C)=[O:28])=[O:23])[CH:19]([CH3:21])[CH3:20])=[O:16].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)[C:4]([CH2:11][CH:12]([CH3:14])[CH3:13])=[C:3]1[C:15]([NH:17][C@H:18]([C:22]([NH:24][CH:25]([C:34](=[O:44])[CH2:35][O:36][C:37]1[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=1)[CH2:26][C:27]([OH:29])=[O:28])=[O:23])[CH:19]([CH3:20])[CH3:21])=[O:16]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 86756360N-[(1-methyl-3-isobutyl-indole-2-cabonyl)valinyl]-3-amino-4-oxo-5-(4-fluorophenyloxy)-pentanoic Acid, tert-butyl Ester

Product 1

HCID 20639713N-[(1-methyl-3-isobutyl-indole-2-cabonyl)valinyl]-3-amino-4-oxo-5-(4-fluorophenyloxy)-pentanoic AcidYield 68%

Procedure

Treatment of the product of Example 84 (72 mg, 0.118 mmol) with TFA as described in Example 80 gave the titled product (42.0 mg, 68%) as a pale yellow powder. MS 30H36FN3O6, [M+Na]+=576, [M−H]−=552. TLC (hexane/EtOAc, 50/50): Rf=0.33.

Sources & evidence

ORD record: ord-72e90768a9734a25834fbf257b9a1c09
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06489353B2

Reaction notes

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