Sodium Hydroxide → [(R)-4-(3-bromo-5-trifluoromethyl-benzenesulfonylamino)-4,5,6,7-tetrahydro-indazol-1-yl]-acetic acid

HRID 1645151Notes

Reaction equation

HRID 1645151 reaction equation
C([O:3][C:4](=[O:30])[CH2:5][N:6]1[C:14]2[CH2:13][CH2:12][CH2:11][C@@H:10]([NH:15][S:16]([C:19]3[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[C:21]([Br:29])[CH:20]=3)(=[O:18])=[O:17])[C:9]=2[CH:8]=[N:7]1)C.[OH-].[Na+]>O1CCCC1>[Br:29][C:21]1[CH:20]=[C:19]([S:16]([NH:15][C@@H:10]2[CH2:11][CH2:12][CH2:13][C:14]3[N:6]([CH2:5][C:4]([OH:30])=[O:3])[N:7]=[CH:8][C:9]2=3)(=[O:18])=[O:17])[CH:24]=[C:23]([C:25]([F:28])([F:26])[F:27])[CH:22]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 44611775HCID 44611775, compound

Product 1

HCID 44611776[(R)-4-(3-bromo-5-trifluoromethyl-benzenesulfonylamino)-4,5,6,7-tetrahydro-indazol-1-yl]-acetic acidYield 78.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [(R)-4-(3-bromo-5-trifluoromethyl-benzenesulfonylamino)-4,5,6,7-tetrahydro-indazol-1-yl]-acetic acid ethyl ester (18.0 mg, 0.035 mmol) in tetrahydrofuran (2 mL) was added an aqueous solution of sodium hydroxide (1 N, 2 mL). The resulting mixture was stirred at room temperature for 2 hours, then extracted with diethyl ether (6 mL). The organic layer was discarded. The aqueous layer was acidified with concentrated hydrochloric acid to pH 4 and then stirred with diethyl ether (2 mL) and petroleum ether (6 mL) at room temperature for 2 hours. The resulting mixture was filtered to afford [(R)-4-(3-bromo-5-trifluoromethyl-benzenesulfonylamino)-4,5,6,7-tetrahydro-indazol-1-yl]-acetic acid (13.3 mg, 78.8%) as a white powder. 1H NMR (400 MHz, CD3OD) δ ppm 8.34 (s, 1 H), 8.20 (s, 2 H), 6.81 (s, 1 H), 4.80 (s, 2 H), 4.48 (t, 1 H), 2.50 (m, 2 H), 2.00-1.72 (m, 4 H). MS calcd. for C16H15BrF3N3O4S 481, obsd. (ESI+) [(M+H)+] 482.

Workup

  1. extractionextracted with diethyl ether (6 mL)
  2. stirringstirred with diethyl ether (2 mL) and petroleum ether (6 mL) at room temperature for 2 hours
  3. filtrationThe resulting mixture was filtered

Sources & evidence

ORD record
ord-42ee92e7194d49079cfcac4cc713317e
Source dataset
uspto-grants-2012_02
Patent number
US08124641B2

Reaction notes

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