Potassium Carbonate → tert-butyl(2S)-2-((3S)-3-{[(6-chloro-2-naphthyl)sulfonyl](2-benzyloxy-2-oxoethyl)amino}-2-oxopyrrolidin-1-yl)propanoate

HRID 7292

Reaction equation

HRID 7292 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([NH:15][C@H:16]1[CH2:20][CH2:19][N:18]([C@@H:21]([CH3:29])[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:17]1=[O:30])(=[O:14])=[O:13])[CH:6]=[CH:5]2.C(=O)([O-])[O-].[K+].[K+].[CH2:37]([O:44][C:45](=[O:48])[CH2:46]Br)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([N:15]([CH2:46][C:45]([O:44][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:48])[C@H:16]1[CH2:20][CH2:19][N:18]([C@@H:21]([CH3:29])[C:22]([O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:23])[C:17]1=[O:30])(=[O:13])=[O:14])[CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 62576Benzyl bromoacetateHCID 69221511tert-butyl(2S)-2-((3S)-3-{[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoate

Product 1

HCID 69329144tert-butyl(2S)-2-((3S)-3-{[(6-chloro-2-naphthyl)sulfonyl](2-benzyloxy-2-oxoethyl)amino}-2-oxopyrrolidin-1-yl)propanoateYield 115.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl (2S)-2-((3S)-3-{[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoate (1 g) in DMF (20 ml) was added potassium carbonate (0.92 g) and benzyl-2-bromoacetate (0.33 g), and the mixture was stirred under nitrogen at room temperature for 72 h. The reaction mixture was filtered, concentrated under reduced pressure, and the residue partitioned between water and DCM. The organic layer was isolated, dried (over magnesium sulphate and purified by SPE (silica, cyclohexane:ethyl acetate 2:1) to give the title compound (1.0 g) as a white solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated under reduced pressure
  3. customthe residue partitioned between water and DCM
  4. customThe organic layer was isolated
  5. dry with materialdried (over magnesium sulphate
  6. custompurified by SPE (silica, cyclohexane:ethyl acetate 2:1)

Sources & evidence

ORD record
ord-41adcde0d5054088a64cf77e9b050dd6
Source dataset
uspto-grants-2006_08
Patent number
US07084139B2

Linked notes

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