Hydrochloric Acid → HCID 58975136, compound

HRID 1178938Notes

Reaction equation

HRID 1178938 reaction equation
C[O:2][C:3](=[O:27])[C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]([CH:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)=[CH:14]2)(=[O:12])=[O:11])=[CH:6][CH:5]=1.[OH-].[Na+].Cl>C1COCC1.CO.O>[CH:22]1([C:15]2[C:16]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:13]([S:10]([C:7]3[CH:8]=[CH:9][C:4]([C:3]([OH:27])=[O:2])=[CH:5][CH:6]=3)(=[O:12])=[O:11])[CH:14]=2)[CH2:23][CH2:24][CH2:25][CH2:26]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58975006HCID 58975006, compound

Product 1

HCID 58975136HCID 58975136, compoundYield 84.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Add to a stirring solution of 4-(3-Cyclopentyl-indole-1-sulfonyl)-benzoic acid methyl ester (2.0 g, 5.22 mmol) in THF (50 mL) and MeOH (25 mL), 5N NaOH (3 mL, 2.9 eq.). Stir the solution for 2 h at room temperature and the remove solvents to give a paste. Treat the paste with 1N HCl (25 mL) and a solid results. Dilute further with water (50 mL). Filter the solid, back-wash with water, and dry (20 mm Hg, 60° C.) to provide the pure title compound (1.63 g, 84%); 1H NMR (DMSO-d6) δ 8.06 (m, 4H), 7.93 (d, J=8.2 Hz, 1H), 7.63 (d, J=7.7 Hz, 1H), 7.53 (s, 1H), 7.37 (t, J=7.7 Hz, 1H), 7.28 (t, J=7.7 Hz, 1H), 3.17 (m, 1H), 2.08 (m, 2H), 1.69 (m, 6H); MS(ESI) m/z 368 (m−H).

Workup

  1. customthe remove solvents to give a paste
  2. customa solid results
  3. filtrationFilter the solid
  4. washback-wash with water
  5. customdry (20 mm Hg, 60° C.)

Sources & evidence

ORD record
ord-eb9401ca96e3496ebcf7f41bcb4d3514
Source dataset
uspto-grants-2007_10
Patent number
US07276516B2

Reaction notes

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