Trifluoroacetic acid → Pyrrolidine-2-carboxylic acid (2'-tert-butylsulfamoyl-3-fluoro-biphenyl-4-yl)-amide

HRID 2217495Notes

Reaction equation

C(OC([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13](=[O:36])[NH:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[S:27](=[O:34])(=[O:33])[NH:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:17][C:16]=1[F:35])=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl.CCOC(C)=O>[C:29]([NH:28][S:27]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[C:18]1[CH:19]=[CH:20][C:15]([NH:14][C:13]([CH:9]2[CH2:10][CH2:11][CH2:12][NH:8]2)=[O:36])=[C:16]([F:35])[CH:17]=1)(=[O:34])=[O:33])([CH3:32])([CH3:30])[CH3:31]

Participants

Conditions

Temperature: 0 °C

Procedure

2-(2′-tert-Butylsulfamoyl-3-fluoro-biphenyl-4-ylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (1.3 g, 2.5 mmol) was dissolved in 40 mL DCM, cooled in an ice bath, added 10 mL trifluoroacetic acid, stirred at 0° C. for 30 minutes then at ambient temperature for one hour. Concentrated solution, redissolved in EtOAc (150 mL), washed with saturated NaHCO3 (2×100 mL), water (100 mL), brine (100 mL), dried with MgSO4, filtered and concentrated to yield title compound as a white solid. (1 g, 91%) APCI (AP−): 418.2 (M−H)−.

Workup

temperaturecooled in an ice bath
waitat ambient temperature for one hour
washwashed with saturated NaHCO3 (2×100 mL), water (100 mL), brine (100 mL)
dry with materialdried with MgSO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-d743b9584c6044c8aa7e6b7c995cb419
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07407974B2

Reaction notes

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