Trifluoroacetic acid → 2-[4'-(4-Fluoro-phenylcarbamoyloxy)-biphenyl-4-sulfonylamino]-3-methyl-butyric acid

HRID 2075835Notes

Reaction equation

HRID 2075835 reaction equation
C([O:5][C:6](=[O:38])[CH:7]([NH:11][S:12]([C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][C:24]([O:27][C:28](=[O:37])[NH:29][C:30]3[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=3)=[CH:23][CH:22]=2)=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH:8]([CH3:10])[CH3:9])(C)(C)C.C(O)(C(F)(F)F)=O>ClC(Cl)C>[F:36][C:33]1[CH:32]=[CH:31][C:30]([NH:29][C:28]([O:27][C:24]2[CH:23]=[CH:22][C:21]([C:18]3[CH:19]=[CH:20][C:15]([S:12]([NH:11][CH:7]([CH:8]([CH3:10])[CH3:9])[C:6]([OH:38])=[O:5])(=[O:14])=[O:13])=[CH:16][CH:17]=3)=[CH:26][CH:25]=2)=[O:37])=[CH:35][CH:34]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67109947HCID 67109947, compound

Product 1

HCID 671108152-[4'-(4-Fluoro-phenylcarbamoyloxy)-biphenyl-4-sulfonylamino]-3-methyl-butyric acidYield 89%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

2-[4′-(4-Fluoro-phenylcarbamoyloxy)-biphenyl-4-sulfonylamino]-3-methyl-butyric acid tert-butyl ester (223 mg) was dissolved in dichloroethane (7.5 mL) and added with TFA (2.5 mL). The mixture was stirred at room temperature for 5 hrs and TLC indicated the reaction was complete. Regular work-up and column chromatography to give 2-[4′-(4-Fluoro-phenylcarbamoyloxy)-biphenyl-4-sulfonylamino]-3-methyl-butyric acid in 89% yield (178 mg).

Sources & evidence

ORD record
ord-57116dfcba784f13b325c59ac1f649f2
Source dataset
uspto-grants-2011_04
Patent number
US07923446B2

Reaction notes

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