Sodium Hydroxide → HCID 44611439, compound

HRID 1966862Notes

Reaction equation

HRID 1966862 reaction equation
C([O:3][C:4](=[O:33])[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]=[CH:23][C:22]([O:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[Cl:32])=[CH:21][CH:20]=3)(=[O:18])=[O:17])[C:9]=2[CH:8]=[N:7]1)C.[OH-].[Na+]>O1CCCC1>[Cl:32][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[O:25][C:22]1[CH:23]=[CH:24][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:33])=[O:3])[N:7]=[CH:8][C:9]2=3)(=[O:17])=[O:18])=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59152968HCID 59152968, compound

Product 1

HCID 44611439HCID 44611439, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of {(R)-4-[4-(2-chloro-phenoxy)-benzenesulfonylamino]-4,5,6,7-tetrahydro-indazol-1-yl}-acetic acid ethyl ester (example 1-1) (167 mg, 0.34 mmol) in tetrahydrofuran (3 mL) was added 1N sodium hydroxide (3 mL). The reaction mixture was stirred at room temperature for 2 hours, and then extracted with diethyl ether (10 mL). The organic layer was discarded. The aqueous layer was acidified with concentrated hydrochloric acid to pH 4 and stirred with diethyl ether (3 mL) and petroleum ether (9 mL) at room temperature for 2 hours. The resulting mixture was filtered through a glass funnel to afford {(R)-4-[4-(2-chloro-phenoxy)-benzenesulfonylamino]-4,5,6,7-tetrahydro-indazol-1-yl}-acetic acid (124 mg, 79%) as a white powder. 1H NMR (400 MHz, CD3OD) δ ppm 7.94 (d, 2 H), 7.60 (q, 1 H), 7.43 (m, 1 H), 7.26 (m, 2 H), 7.07 (d, 2 H), 6.70 (s, 1 H), 4.80 (s, 2 H), 4.37 (t, 1 H), 2.60-2.48 (m, 2 H), 1.94-1.75 (m, 4 H). MS cald. (calculated) for C21H20ClN3O5S 461, obsd. (observed) (ESI+) [(M+H)+] 462.

Workup

  1. extractionextracted with diethyl ether (10 mL)
  2. stirringstirred with diethyl ether (3 mL) and petroleum ether (9 mL) at room temperature for 2 hours
  3. filtrationThe resulting mixture was filtered through a glass funnel

Sources & evidence

ORD record
ord-bfe2cbe031cb4359b351ad998960cd37
Source dataset
uspto-grants-2013_04
Patent number
US08420675B2

Reaction notes

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