Tetrahydrofuran → HCID 58975077, compound

HRID 736986Notes

Reaction equation

HRID 736986 reaction equation
C[O:2][C:3](=[O:28])[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[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)=[CH:14]2)(=[O:12])=[O:11])=[CH:6][CH:5]=1.C1COCC1.[OH-].[Na+]>CO>[O:25]1[CH2:24][CH2:23][CH:22]([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:6]=[CH:5][C:4]([C:3]([OH:28])=[O:2])=[CH:9][CH:8]=3)(=[O:12])=[O:11])[CH:14]=2)[CH2:27][CH2:26]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 58975195HCID 58975195, compound

Product 1

HCID 58975077HCID 58975077, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add to a suspension of 4-[3-(tetrahydro-pyran-4-yl)-indole-1-sulfonyl]-benzoic acid methyl ester (16.7 g, 41.83 mmol) in methanol (200 mL) with stirring THF (600 mL). Treat the solution with 5N NaOH (23.5 ml, 2.8 eq.) and stir for 2 h at room temperature. Concentrate the solution to near dryness and treat with 1N HCl (125 mL), a solid separates. Dilute to 500 mL total volume with water, filter, back-wash with water, and dry (20 mm Hg, 60° C.) to give a resulting solid found to be pure title compound (15.8 g, 98%); 1H NMR (DMSO-d6) 13.57 (s, 1H), 8.08 (m, 4H), 7.93 (d, J=8.2 Hz, 1H), 7.68 (d, J=8.2 Hz, 1H), 7.57 (s, 1H), 7.37 (t, J=8.2 Hz, 1H), 7.27 (t, J=7.1 Hz, 1H), 3.95 (m, 2H), 3.47 (t, J=12.0 Hz, 2H), 3.03 (m, 1H), 1.85 (m, 2H), 1.70 (m, 2H); MS (ESI) m/z 384 (m−H).

Workup

  1. concentrationConcentrate the solution
  2. additiontreat with 1N HCl (125 mL)
  3. additionDilute to 500 mL total volume with water
  4. filtrationfilter
  5. washback-wash with water
  6. customdry (20 mm Hg, 60° C.)
  7. customto give a resulting solid

Sources & evidence

ORD record
ord-d62a2e4c4b4f4e89809ef9a3dda6aa1b
Source dataset
uspto-grants-2009_09
Patent number
US07595339B2

Reaction notes

Loading…