Water → HCID 66877113, compound

HRID 503927Notes

Reaction equation

HRID 503927 reaction equation
[CH2:1]([S-:3])[CH3:2].[Na+].[C:5]([O:9][C:10]([N:12]1[CH2:16][CH2:15][CH:14]([C:17]2[CH:22]=[CH:21][C:20]([S:23]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28](Cl)[CH:27]=3)(=[O:25])=[O:24])=[CH:19][C:18]=2[O:33][CH3:34])[CH2:13]1)=[O:11])([CH3:8])([CH3:7])[CH3:6].O>CN(C=O)C>[C:5]([O:9][C:10]([N:12]1[CH2:16][CH2:15][CH:14]([C:17]2[CH:22]=[CH:21][C:20]([S:23]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([S:3][CH2:1][CH3:2])[CH:27]=3)(=[O:25])=[O:24])=[CH:19][C:18]=2[O:33][CH3:34])[CH2:13]1)=[O:11])([CH3:8])([CH3:7])[CH3:6].[C:5]([O:9][C:10]([N:12]1[CH2:16][CH2:15][CH:14]([C:17]2[CH:22]=[CH:21][C:20]([S:23]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([S:3][CH2:1][CH3:2])[CH:27]=3)(=[O:24])=[O:25])=[CH:19][C:18]=2[OH:33])[CH2:13]1)=[O:11])([CH3:6])([CH3:8])[CH3:7]

Participants

6

Reactant 3

HCID 962WaterHCID 4459711Sodium ethanethiolateHCID 66877481HCID 66877481, compound

Product 2

HCID 66877113HCID 66877113, compoundHCID 66877148HCID 66877148, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Sodium ethanethiolate (0.698 g, 8.304 mmol) was added to a solution of 3-[4-(3-chloro-benzenesulfonyl)-2-methoxy-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (1.251 g, 2.768 mmol) in DMF (10 mL) and the mixture was heated at 100° C. for 48 hours. The reaction mixture was cooled to room temperature and water was added. The resulting mixture was extracted with EtOAc, and the combined organic extracts were washed with water brine, dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified via flash chromatography (hexane/EtOAc/AcOH, 70/30/1) to give 3-[4-(3-ethylsulfanyl-benzenesulfonyl)-2-methoxy-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester as a first fraction, and 3-[4-(3-ethylsulfanyl-benzenesulfonyl)-2-hydroxy-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester as a second fraction.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionThe resulting mixture was extracted with EtOAc
  3. washthe combined organic extracts were washed with water brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified via flash chromatography (hexane/EtOAc/AcOH, 70/30/1)

Sources & evidence

ORD record
ord-4e03c757464d434e9959d87d3f57ecbf
Source dataset
uspto-grants-2010_08
Patent number
US07776910B2

Reaction notes

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