(1S)-2-Chloro-1-methyl-2-oxoethyl acetate → HCID 68663433, compound

HRID 452655Notes

Reaction equation

HRID 452655 reaction equation
[Br:1][C:2]1[C:6]2[CH:7]=[C:8]([C:11]([NH:13][NH2:14])=[O:12])[CH:9]=[CH:10][C:5]=2[O:4][CH:3]=1.[C:15]([O:18][C@@H:19]([CH3:23])[C:20](Cl)=[O:21])(=[O:17])[CH3:16]>CN(C)C(=O)C.C(OCC)(=O)C>[C:15]([O:18][C@@H:19]([CH3:23])[C:20]([NH:14][NH:13][C:11]([C:8]1[CH:9]=[CH:10][C:5]2[O:4][CH:3]=[C:2]([Br:1])[C:6]=2[CH:7]=1)=[O:12])=[O:21])(=[O:17])[CH3:16]

Participants

5

Reactant 2

HCID 11094804(1S)-2-Chloro-1-methyl-2-oxoethyl acetateHCID 44481755HCID 44481755, compound

Product 1

HCID 68663433HCID 68663433, compoundYield 89.2%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

To a solution of 3-bromo-1-benzofuran-5-carbohydrazide (2.64 g, 10.35 mmol) in N,N-dimethylacetamide (10 mL) was added dropwise (1S)-2-chloro-1-methyl-2-oxoethyl acetate (1.44 mL, 11.38 mmol) at 0° C., and the resulting mixture was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was recrystallized from hexane/ethyl acetate to give the title compound (3.41 g, yield 89%) as colorless crystals.

Workup

  1. washwashed with water and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was recrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-dbbf6dbb069949f1b633e45d1570ab04
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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