Hypochlorite → HCID 54219271, compound

HRID 1632934Notes

Reaction equation

HRID 1632934 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:15][NH:14][C:13]1=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:17][O-].[Na+].Cl[O-]>ClCCl.O>[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:15][N:14]([Cl:17])[C:13]1=[O:16])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 61739HypochloriteHCID 12834624benzyl N-[(3S)-2-oxoazetidin-3-yl]carbamateHCID 23665760Sodium Hypochlorite

Product 1

HCID 54219271HCID 54219271, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of (S)-3-benzyloxycarbonylamino-2-azetidinone (440 mg) in dichloromethane (15 ml) was combined with a solution of borax (1.53 g) in water (10 ml) and cooled in an ice-bath to 0°-5° C. While stirring vigorously, a 5.07% solution of sodium hypochlorite (3.2 ml) was added; after 1 hour another portion (1.6 ml) of hypochlorite solutionwas added and stirring was continued for 1 hour at 0°-5° C. The organic layer was separated and the aqueous solution was extracted with dichloromethane. The combined extracts were dried (sodium sulfate) and solvent was removed in vacuo giving (S)-3-benzyloxycarbonylamino-1-chloroazetidin-2-one as an oil.

Workup

  1. temperaturecooled in an ice-bath to 0°-5° C
  2. stirringstirring
  3. customThe organic layer was separated
  4. extractionthe aqueous solution was extracted with dichloromethane
  5. dry with materialThe combined extracts were dried (sodium sulfate) and solvent
  6. customwas removed in vacuo

Sources & evidence

ORD record
ord-7effe33f761a451a909e851cf3b2d47d
Source dataset
uspto-grants-1984_10
Patent number
US04478749

Reaction notes

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