Benzyl chloroformate → cis-3-Benzyloxycarbonylamino-4-oxo-2-p-toluenesulfonyloxymethylazetidine

HRID 2050400Notes

Reaction equation

[NH2:1][C@H:2]1[C:5](=[O:6])[NH:4][C@H:3]1[CH2:7][O:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1)(=[O:11])=[O:10].Cl[C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21].N([C@H]1C(=O)N(CC2C=CC(OC)=CC=2OC)[C@H]1C(OC)=O)=[N+]=[N-].O(CC(Cl)=O)C1C=CC=CC=1>>[CH2:23]([O:22][C:20]([NH:1][C@H:2]1[C:5](=[O:6])[NH:4][C@H:3]1[CH2:7][O:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1)(=[O:11])=[O:10])=[O:21])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

Reactant 4

HCID 10387Benzyl chloroformate

HCID 69703Phenoxyacetyl chloride

HCID 86734328Methyl cis-1-(2,4-dimethoxybenzyl)-3-azido-4-oxoazetidine-2-carboxylate

HCID 86734334cis-3-Amino-4-oxo-2-p-toluenesulfonyloxymethylazetidine

Product 1

HCID 86736961cis-3-Benzyloxycarbonylamino-4-oxo-2-p-toluenesulfonyloxymethylazetidine

Procedure

Reaction of cis-3-amino-4-oxo-2-p-toluenesulfonyloxymethylazetidine with benzyl chloroformate according to the procedure described in Preparation 2 for reaction of methyl cis-3-azido-1-(2,4-dimethoxybenzyl)-4-oxoazetidine-2-carboxylate and phenoxyacetyl chloride gives cis-3-benzyloxycarbonylamino-4-oxo-2-p-toluenesulfonyloxymethylazetidine.

Sources & evidence

ORD record: ord-fc1b09b81c364fcda19e9b16304d3c16
Source dataset: uspto-grants-1980_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04200572

Reaction notes

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