Hydrochloric Acid → HCID 58975136, compound

HRID 1178956Notes

Reaction equation

HRID 1178956 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>[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

5

Reactant 3

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

Product 1

HCID 58975136HCID 58975136, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 12 L RBF, charge 4-(3-cyclopentyl-indole-1-sulfonyl)-benzoic acid methyl ester (465 g 1.213 mol) and THF (4.7 L). Add 5N NaOH (485 ml) dropwise at ambient temperature. Stir the solution at room temperature overnight. Bring the pH of the reaction to 1 with c.HCl. Separate the layers and extract the aqueous layer with ethyl acetate (4 L). Dry the combined organic layers over sodium sulfate, filter and rinse with ethyl acetate. Concentrate the organics under vacuum to give an off-white solid (401 g, yield=89.5%) of the title compound.

Workup

  1. customBring the pH of the reaction to 1 with c
  2. customSeparate the layers
  3. extractionextract the aqueous layer with ethyl acetate (4 L)
  4. dry with materialDry the combined organic layers over sodium sulfate
  5. filtrationfilter
  6. washrinse with ethyl acetate
  7. concentrationConcentrate the organics under vacuum

Sources & evidence

ORD record
ord-d28f3968eca54db1b4354a94e57a68ac
Source dataset
uspto-grants-2007_10
Patent number
US07276516B2

Reaction notes

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