Water → HCID 69338013, compound

HRID 1063450Notes

Reaction equation

HRID 1063450 reaction equation
[C:1]([O:4][CH2:5][C@H:6]([CH3:18])[CH2:7][CH:8]([NH:14][C:15](=[O:17])[CH3:16])[C:9]1[S:10][CH:11]=[CH:12][CH:13]=1)(=[O:3])[CH3:2].[Br:19]N1C(=O)CCC1=O.O>CN(C)C=O>[C:1]([O:4][CH2:5][C@H:6]([CH3:18])[CH2:7][CH:8]([NH:14][C:15](=[O:17])[CH3:16])[C:9]1[S:10][C:11]([Br:19])=[CH:12][CH:13]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 69337972HCID 69337972, compound

Product 1

HCID 69338013HCID 69338013, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(2R)-Acetylamino-2-methyl-4-(thiophen-2-yl)butyl acetate (1.81 g, 6.70 mmol) obtained in Example 47 (b) was dissolved in dimethylformamide (20 ml), and N-bromosuccinimide (1.27 g, 7.11 mmol) was added thereto in an ice bath followed by stirring under a nitrogen atmosphere for 10 minutes in an ice bath and then overnight at room temperature. The reaction solution was poured into water, extracted with ethyl acetate, and the ethyl acetate layer was washed with a saturated aqueous sodium chloride solution. The ethyl acetate layer was dried over anhydrous sodium sulfate, and the solvent was evaporated in vacuo. The residue was purified by chromatography on a silica gel column (elution solvent; hexane:ethyl acetate=3:1-1:2) to afford the title compound (2.32 g, 99% yield).

Workup

  1. customin an ice bath followed
  2. customovernight
  3. customat room temperature
  4. extractionextracted with ethyl acetate
  5. washthe ethyl acetate layer was washed with a saturated aqueous sodium chloride solution
  6. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulfate
  7. customthe solvent was evaporated in vacuo
  8. customThe residue was purified by chromatography on a silica gel column (elution solvent; hexane:ethyl acetate=3:1-1:2)

Sources & evidence

ORD record
ord-9ac2052d894c4621b0a0873695aae260
Source dataset
uspto-grants-2005_11
Patent number
US06964976B2

Reaction notes

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