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

HRID 349513Notes

Reaction equation

HRID 349513 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+].Br[CH2:38][C:39]([NH2:41])=[O:40]>CN(C=O)C>[NH2:41][C:39](=[O:40])[CH2:38][N:15]([S:12]([C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([Cl:1])[CH:3]=2)[CH:8]=1)(=[O:13])=[O:14])[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]

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 696322-Bromoacetamide2×HCID 69221511tert-butyl(2S)-2-((3S)-3-{[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoate

Product 1

HCID 69223739tert-Butyl (2S)-2-((3S)-3-{(2-amino-2-oxoethyl)[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoateYield 94.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of tert-butyl (2S)-2-((3S)-3-{[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoate (1.31 g) in DMF (22 ml) was treated with potassium carbonate (0.786 g) followed by 2-bromoacetamide (0.48 g) and the resultant mixture stirred at room temperature for 22 h. Additional 2-bromoacetamide (0.4 g) and potassium carbonate (0.4 g) were added and the mixture was stirred at room temperature for 24 h. The reaction mixture was evaporated under reduced pressure and the residue partitioned between ethyl acetate and water. The separated organic layer was washed with water, dried (over magnesium sulphate) and evaporated under reduced pressure to give the title compound (1.4 g) as a white foam.

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. customthe residue partitioned between ethyl acetate and water
  3. washThe separated organic layer was washed with water
  4. dry with materialdried (over magnesium sulphate)
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-bf751a7409384fa19df0e81ef715fc61
Source dataset
uspto-grants-2007_02
Patent number
US07179835B2

Reaction notes

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