Chloroacetyl chloride → HCID 67767539, compound

HRID 361569Notes

Reaction equation

HRID 361569 reaction equation
[O:1]([C:8]([NH:10][C:11]1[CH:32]=[CH:31][C:14]([CH2:15][N:16]2[C:22](=[O:23])[C@H:21]3[CH2:24][CH2:25][CH2:26][C@H:20]3[NH:19][C:18]3[CH:27]=[CH:28][CH:29]=[CH:30][C:17]2=3)=[CH:13][CH:12]=1)=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:33][CH2:34][C:35](Cl)=[O:36]>CN(C=O)C.C([O-])(O)=O.[Na+]>[Cl:33][CH2:34][C:35]([N:19]1[C@@H:20]2[CH2:26][CH2:25][CH2:24][C@@H:21]2[C:22](=[O:23])[N:16]([CH2:15][C:14]2[CH:31]=[CH:32][C:11]([NH:10][C:8]([O:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[O:9])=[CH:12][CH:13]=2)[C:17]2[CH:30]=[CH:29][CH:28]=[CH:27][C:18]1=2)=[O:36]

Participants

5

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 67767670HCID 67767670, compound

Product 1

HCID 67767539HCID 67767539, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of (3aR*,10aS*)-9-[4-(phenoxycarbonylamino)benzyl]-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one (1.61 g, 3.8 mmol) in DMF (20 mL) was added chloroacetyl chloride (0.36 mL, 4.5 mmol) and the mixture was stirred at room temperature for 2 hours. This reaction mixture was diluted with saturated aqueous NaHCO3 solution and extracted with 3 portions of chloroform. The pooled organic layer was washed with 2 portions of water and, then, with saturated aqueous NaCl solution. This solution was dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was crystallized from chloroform-diethyl ether to provide 0.90 g (yield 47%) of the compound. m.p. 207-210° C.

Workup

  1. extractionextracted with 3 portions of chloroform
  2. washThe pooled organic layer was washed with 2 portions of water
  3. dry with materialThis solution was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was crystallized from chloroform-diethyl ether

Sources & evidence

ORD record
ord-d6c3390377dc4b8c8b7a979607b6174b
Source dataset
uspto-grants-1999_02
Patent number
US05866567

Reaction notes

Loading…