Ethyl Acetate → HCID 86588221, compound

HRID 1814326Notes

Reaction equation

HRID 1814326 reaction equation
[C:1]([O:5][C:6](=[O:39])[CH2:7][CH:8]([NH:15][S:16]([C:19]1[CH:24]=[CH:23][C:22](F)=[CH:21][C:20]=1[O:26][CH2:27][CH2:28][C:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=[CH:31][CH:30]=1)(=[O:18])=[O:17])[C:9]([N:11]([O:13][CH3:14])[CH3:12])=[O:10])([CH3:4])([CH3:3])[CH3:2].CCOC(C)=O.[NH:46]1[CH2:50][CH2:49][CH2:48][CH2:47]1>>[C:1]([O:5][C:6](=[O:39])[CH2:7][C@H:8]([NH:15][S:16]([C:19]1[CH:24]=[CH:23][C:22]([N:46]2[CH2:50][CH2:49][CH2:48][CH2:47]2)=[CH:21][C:20]=1[O:26][CH2:27][CH2:28][C:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=[CH:31][CH:30]=1)(=[O:18])=[O:17])[C:9]([N:11]([O:13][CH3:14])[CH3:12])=[O:10])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 8857Ethyl AcetateHCID 31268PyrrolidineHCID 131724822HCID 131724822, compound

Product 1

HCID 86588221HCID 86588221, compoundYield 81%

Procedure

A solution of S)-3-[4-fluoro-2-(2-naphthalen-1-yl-ethoxy)-benzenesulfonyl amino]-N-methoxy-N methyl-succinamic acid tert-butyl ester (1.10 g, 2.0 mmol) in pyrollidine (10 mL) was heated at 50° C. for 5 h. The reaction mixture was allowed to cool and then was added EtOAc (150 mL). The resulting solution was washed sequentially with the following solutions: 5% citric acid, saturated NaHCO3, and brine. The organic phase was dried (MgSO4), and then the solvent was removed under vacuum. The resulting crude product was purified using flash silica gel chromatography (25% EtOAc in hexanes). (S)-N-Methoxy-N-methyl-3-[2-(2-naphthalen-1-yl-ethoxy)-4-pyrrolidin-1-yl-benzenesulfonyl amino]-succinamic acid tert-butyl ester was obtained in 81% yield (1.0 g) as a off white foam. MS (APCI) m/z 610.3 (M−1).

Workup

  1. temperatureto cool
  2. washThe resulting solution was washed sequentially with the following solutions
  3. dry with materialThe organic phase was dried (MgSO4)
  4. customthe solvent was removed under vacuum
  5. customThe resulting crude product was purified

Sources & evidence

ORD record
ord-3a261d9ec1834eebb6f29cc0ae2a212e
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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