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

HRID 2297059Notes

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:23]([NH:25][CH:26]([C:35](=[O:48])[CH2:36][O:37][C:38]1[C:43]([F:44])=[C:42]([F:45])[CH:41]=[C:40]([F:46])[C:39]=1[F:47])[CH2:27][C:28]([O:30]C(C)(C)C)=[O:29])=[O:24])[CH2:19][CH:20]([CH3:22])[CH3:21])=[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:23]([NH:25][CH:26]([C:35](=[O:48])[CH2:36][O:37][C:38]1[C:43]([F:44])=[C:42]([F:45])[CH:41]=[C:40]([F:46])[C:39]=1[F:47])[CH2:27][C:28]([OH:30])=[O:29])=[O:24])[CH2:19][CH:20]([CH3:21])[CH3:22])=[O:16]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 86756363N-[(1-methyl-3-isobutyl-indole-2-cabonyl)leucinyl]-3-amino-4-oxo-5-(2,3,5,6-tetrafluorophenyloxy)-pentanoic acid, tert-butyl ester

Product 1

HCID 20639708N-[(1-methyl-3-isobutyl-indole-2-cabonyl)leucinyl]-3-amino-4-oxo-5-(2,3,5,6-tetrafluorophenyloxy)-pentanoic AcidYield 67%

Procedure

Treatment of N-[(1-methyl-3-isobutyl-indole-2-cabonyl)leucinyl]-3-amino-4-oxo-5-(2,3,5,6-tetrafluorophenyloxy)-pentanoic acid, tert-butyl ester (47.6 mg, 0.070 mmol) with TFA as described in Example 80 gave the titled product (29.0 mg, 67%) as a white powder. MS C35H43F4N3O6, [M+Na]+=644, [M−H]−=620. TLC (CH2Cl2/MeOH, 90/10): Rf=0.19.

Sources & evidence

ORD record: ord-c8b9e24bd1f2453291b7b9c07b8c881b
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06489353B2

Reaction notes

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