Hydrochloric Acid → HCID 58975084, compound

HRID 1178947Notes

Reaction equation

HRID 1178947 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:31])[C:6]1[CH:11]=[CH:10][C:9]([S:12]([N:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([CH:24]3[CH2:28][CH2:27][C:26]([F:30])([F:29])[CH2:25]3)=[CH:16]2)(=[O:14])=[O:13])=[CH:8][CH:7]=1.Cl.CCOC(C)=O>C1COCC1.CO>[F:30][C:26]1([F:29])[CH2:27][CH2:28][CH:24]([C:17]2[C:18]3[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:15]([S:12]([C:9]3[CH:8]=[CH:7][C:6]([C:5]([OH:31])=[O:4])=[CH:11][CH:10]=3)(=[O:14])=[O:13])[CH:16]=2)[CH2:25]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 58975223HCID 58975223, compound

Product 1

HCID 58975084HCID 58975084, compoundYield 93.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Add aqueous sodium hydroxide (5N, 0.72 ml, 3 eq) to a solution of 4-[3-(3,3-Difluoro-cyclopentyl)-indole-1-sulfonyl]-benzoic acid methyl ester (500 mg, 1.20 mml, 1 eq) in 5 ml THF, 2.5 ml MeOH. Stir reaction at room temperature for 2 hours. Remove solvent on rotovap and add 1N HCl and EtOAc. Extract products into organics, separate organics, and then dry organics with MgSO4. Filter off drying agent, and remove organics on rotovap to give 4-[3-(3,3-Difluoro-cyclopentyl)-indole-1-sulfonyl]-benzoic acid (450 mg, 92% yield) which was used without further purification.

Workup

  1. customreaction at room temperature for 2 hours
  2. customExtract products into organics, separate organics
  3. filtrationFilter off
  4. customdrying agent
  5. customremove organics on rotovap

Sources & evidence

ORD record
ord-78074bb207d14fb1a6376a3eb92636eb
Source dataset
uspto-grants-2007_10
Patent number
US07276516B2

Reaction notes

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