Trifluoroacetic acid → HCID 20639705, compound

HRID 634943Notes

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]([N:17]([CH:51]1[CH2:56][CH2:55][CH2:54][CH2:53][CH2:52]1)[C@H:18]([C:20]([NH:22][CH:23]([C:32](=[O:50])[CH2:33][O:34][C:35]1[N:39]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[N:38]=[C:37]([C:46]([F:49])([F:48])[F:47])[CH:36]=1)[CH2:24][C:25]([O:27]C(C)(C)C)=[O:26])=[O:21])[CH3:19])=[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]([N:17]([CH:51]1[CH2:52][CH2:53][CH2:54][CH2:55][CH2:56]1)[C@H:18]([C:20]([NH:22][CH:23]([C:32](=[O:50])[CH2:33][O:34][C:35]1[N:39]([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[N:38]=[C:37]([C:46]([F:49])([F:48])[F:47])[CH:36]=1)[CH2:24][C:25]([OH:27])=[O:26])=[O:21])[CH3:19])=[O:16]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 86756368HCID 86756368, compound

Product 1

HCID 20639705HCID 20639705, compoundYield 48%

Procedure

Treatment of N-[(1-methyl-3-isobutyl-indole-2-carbonyl)cyclohexylalaninyl]-3-amino-4-oxo-5-[1-phenyl3-(trifluoromethyl)pyrazol-5-yloxy]-pentanoic acid, tert-butyl ester (55 mg, 0.071 mmol) with TFA as described in Example 80 gave the titled product (24.6 mg, 48%) as a white powder. MS C38H44F4N5O6, [M+H]+ =746, [M−H]− =722. TLC (CH2Cl2/MeOH, 90/10): Rf=0.26.

Sources & evidence

ORD record: ord-0407b4201d814694a4e948a806a11f42
Source dataset: uspto-grants-2001_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06184244B2

Reaction notes

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