Sodium Hydroxide → HCID 44815647, compound

HRID 1696883Notes

Reaction equation

HRID 1696883 reaction equation
C([O:5][C:6](=[O:38])[CH2:7][O:8][C:9]1[C:18]2[CH2:17][CH2:16][CH2:15][C@@H:14]([NH:19][S:20]([C:23]3[CH:28]=[CH:27][C:26]([O:29][C:30]4[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=4)=[C:25]([Cl:37])[CH:24]=3)(=[O:22])=[O:21])[C:13]=2[CH:12]=[CH:11][CH:10]=1)(C)(C)C.[OH-].[Na+]>O1CCCC1>[Cl:37][C:25]1[CH:24]=[C:23]([S:20]([NH:19][C@@H:14]2[CH2:15][CH2:16][CH2:17][C:18]3[C:9]([O:8][CH2:7][C:6]([OH:38])=[O:5])=[CH:10][CH:11]=[CH:12][C:13]2=3)(=[O:21])=[O:22])[CH:28]=[CH:27][C:26]=1[O:29][C:30]1[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59192628HCID 59192628, compound

Product 1

HCID 44815647HCID 44815647, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-{5-[3-chloro-4-(4-chloro-phenoxy)benzenesulfonylamino]-5,6,7,8-tetrahydro-naphthalen-1-yloxy}-acetic acid tert-butyl ester (160 mg, 0.277 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 precipitate was collected by filtering through a glass funnel to afford (R)-{5-[3-chloro-4-(4-chloro-phenoxy)-benzenesulfonylamino]-5,6,7,8-tetrahydro-naphthalen-1-yloxy}-acetic acid (114 mg, 79%) as a white powder. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.21 (d, J=8.59 Hz, 1H), 8.02 (d, J=2.27 Hz, 1H), 7.82 (dd, J=8.59, 2.27 Hz, 1H), 7.53 (d, J=8.84 Hz, 2H), 7.13-7.23 (m, 2H), 7.05 (t, J=8.08 Hz, 1H), 6.67 (dd, J=11.75, 7.96 Hz, 2H), 4.65 (s, 2H), 4.39 (d, J=8.08 Hz, 1H), 1.78 (m, 2H), 1.59 (m, 4H); MS cald. For C24H21Cl2NO6S 521, obsd. 522 (ESI+) [(M+H)+].

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. customThe precipitate was collected
  4. filtrationby filtering through a glass funnel

Sources & evidence

ORD record
ord-19ebf6a4d5f74f88bfb2846f366a55b7
Source dataset
uspto-grants-2012_04
Patent number
US08163781B2

Reaction notes

Loading…