Potassium Carbonate → HCID 66877432, compound

HRID 503949Notes

Reaction equation

HRID 503949 reaction equation
Br[CH2:2][C:3]([O:5][CH3:6])=[O:4].C(=O)([O-])[O-].[K+].[K+].[C:13]([O:17][C:18]([N:20]1[CH2:24][CH2:23][CH:22]([C:25]2[CH:30]=[CH:29][C:28]([S:31]([C:34]3[CH:39]=[CH:38][CH:37]=[C:36]([F:40])[CH:35]=3)(=[O:33])=[O:32])=[CH:27][C:26]=2[OH:41])[CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14]>CC(C)=O>[C:13]([O:17][C:18]([N:20]1[CH2:24][CH2:23][CH:22]([C:25]2[CH:30]=[CH:29][C:28]([S:31]([C:34]3[CH:39]=[CH:38][CH:37]=[C:36]([F:40])[CH:35]=3)(=[O:33])=[O:32])=[CH:27][C:26]=2[O:41][CH2:2][C:3]([O:5][CH3:6])=[O:4])[CH2:21]1)=[O:19])([CH3:16])([CH3:14])[CH3:15]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 66877230HCID 66877230, compound

Product 1

HCID 66877432HCID 66877432, compoundYield 103.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Methyl bromoacetate (47 L, 0.495 mmol), followed by potassium carbonate (136.7 mg, 0.99 mmol) were added to a solution of 3-[4-(3-fluoro-benzenesulfonyl)-2-hydroxy-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (198.7 mg, 0.471 mmol) in acetone (5 mL) under argon atmosphere. The reaction mixture was stirred at room temperature for 4 hours, then filtered and the solvent was evaporated under reduced pressure to give 240.9 mg of 3-[4-(3-fluoro-benzenesulfonyl)-2-methoxycarbonylmethoxy-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester, which was used without further purification in the next step.

Workup

  1. filtrationfiltered
  2. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-5d418e3cedb04c18aa3a515d454df319
Source dataset
uspto-grants-2010_08
Patent number
US07776910B2

Reaction notes

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