Dimethylformamide → HCID 66673350, compound

HRID 1869652Notes

Reaction equation

HRID 1869652 reaction equation
[C:1]([O:4][CH2:5][C@@:6]([NH:19][C:20](=[O:22])[CH3:21])([CH3:18])[CH2:7][CH2:8][C:9]1[O:10][C:11]([C:14]#[C:15][CH2:16]Br)=[CH:12][CH:13]=1)(=[O:3])[CH3:2].[Cl-:23].[NH4+].CN(C)[CH:27]=[O:28]>O.C(OCC)(=O)C>[C:1]([O:4][CH2:5][C@@:6]([NH:19][C:20](=[O:22])[CH3:21])([CH3:18])[CH2:7][CH2:8][C:9]1[O:10][C:11]([C:14]#[C:15][CH2:16][O:28][C:27]2[CH:9]=[CH:8][C:7]([Cl:23])=[CH:6][CH:5]=2)=[CH:12][CH:13]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 66672508HCID 66672508, compound

Product 1

HCID 66673350HCID 66673350, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Subsequently, to the reaction mixture was added a solution of (2R)-1-acetoxy-2-acetylamino-2-methyl-4-[5-(3-bromoprop-1-ynyl)furan-2-yl]butane (0.3050 g, 0.82 mmol) obtained in Example (22b) in N,N-dimethylformamide (4 ml) with stirring under ice-cooling, and then the resulting mixture was stirred at room temperature for 30 minutes. After stirring, saturated aqueous ammonium chloride solution was added to the reaction mixture to quench the reaction, and then the reaction mixture was diluted with water and ethyl acetate and extracted with ethyl acetate. The extract was washed successively with water and saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. After filtration, the solvent was removed in vacuo, and the residue was purified by chromatography on a silica gel column using a mixed solvent of dichloromethane and acetone (10:1) as the eluent to afford the title compound (0.3188 g, yield: 93%).

Workup

  1. temperaturecooling
  2. stirringthe resulting mixture was stirred at room temperature for 30 minutes
  3. stirringAfter stirring
  4. customto quench
  5. customthe reaction
  6. extractionextracted with ethyl acetate
  7. washThe extract was washed successively with water and saturated aqueous sodium chloride solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationAfter filtration
  10. customthe solvent was removed in vacuo
  11. customthe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-329245b417f94b04b88cf20d0c0e9dd6
Source dataset
uspto-grants-2009_12
Patent number
US07638551B2

Reaction notes

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