Acetyl chloride → 1-(Benzyloxycarbonyldiethylphosphono)methyl-3-azido-4-chloro-2-azetidinone

HRID 903190Notes

Reaction equation

HRID 903190 reaction equation
[CH2:1]([O:8][C:9]([CH2:11][CH2:12][O:13][P:14]([CH2:19][N:20]1[CH:23](S(C)(=O)=O)[CH:22]([N:28]=[N+:29]=[N-:30])[C:21]1=[O:31])([O:16][CH2:17][CH3:18])=[O:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Cl:35])(=O)C>>[CH2:1]([O:8][C:9]([CH2:11][CH2:12][O:13][P:14]([CH2:19][N:20]1[CH:23]([Cl:35])[CH:22]([N:28]=[N+:29]=[N-:30])[C:21]1=[O:31])([O:16][CH2:17][CH3:18])=[O:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 6367Acetyl chlorideHCID 867372511-(Benzyloxycarbonyldiethylphosphono)methyl-3-azido-4-methylsulfonyl-2-azetidinone

Product 1

HCID 867372531-(Benzyloxycarbonyldiethylphosphono)methyl-3-azido-4-chloro-2-azetidinone

Procedure

1-(Benzyloxycarbonyldiethylphosphono)methyl-3-azido-4-methylsulfonyl-2-azetidinone (0.446 g.) is dissolved in acetyl chloride (5 ml.). The mixture is allowed to stand for 10 minutes and the acetyl chloride is removed under reduced pressured to afford 1-(benzyloxycarbonyldiethylphosphono)methyl-3-azido-4-chloro-2-azetidinone.

Workup

  1. customthe acetyl chloride is removed

Sources & evidence

ORD record
ord-14df11bc91e64d2684f62d28aeb987fc
Source dataset
uspto-grants-1980_10
Patent number
US04226866

Reaction notes

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