Dichloromethane → (3S,4R)-4-(4-p-nitrobenzyloxycarbonylaminobutyrylthio)-3-methoxy-2-oxoazetidine

HRID 2309097Notes

Reaction equation

HRID 2309097 reaction equation
[Na+].[N+:2]([C:5]1[CH:21]=[CH:20][C:8]([CH2:9][O:10][C:11]([NH:13][CH2:14][CH2:15][CH2:16][C:17]([O-:19])=[S:18])=[O:12])=[CH:7][CH:6]=1)([O-:4])=[O:3].C(O[C@@H:26]1[NH:29][C:28](=[O:30])[C@H:27]1[O:31][CH3:32])(=O)C.O1CCOCC1.C(Cl)Cl>P([O-])([O-])([O-])=O>[N+:2]([C:5]1[CH:21]=[CH:20][C:8]([CH2:9][O:10][C:11]([NH:13][CH2:14][CH2:15][CH2:16][C:17]([S:18][C@H:26]2[NH:29][C:28](=[O:30])[C@@H:27]2[O:31][CH3:32])=[O:19])=[O:12])=[CH:7][CH:6]=1)([O-:4])=[O:3]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 312751,4-DioxaneHCID 56607243(3S,4S)-4-acetoxy-3-methoxy-2-oxoazetidineHCID 178523351HCID 178523351, compound

Product 1

HCID 18609679(3S,4R)-4-(4-p-nitrobenzyloxycarbonylaminobutyrylthio)-3-methoxy-2-oxoazetidine

Reagents, catalysts & solvents 1

HCID 1061PhosphateSolvent

Procedure

Analogously to Example 55b), an aqueous solution of 480 mg of 4-p-nitrobenzyloxycarbonylaminothiobutyric acid sodium salt is added to 159 mg of (3S,4S)-4-acetoxy-3-methoxy-2-oxoazetidine in 6 ml of a phosphate buffer of a pH of 7 and 0.4 ml of dioxan. After working up and chromatography over silica gel, the title compound with the following IR spectrum (CH2Cl2) is obtained:

Sources & evidence

ORD record
ord-38b4a659740f4b74a116434e886f708e
Source dataset
uspto-grants-1987_09
Patent number
US04692442

Reaction notes

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