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

HRID 1710256Notes

Reaction equation

HRID 1710256 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].Cl[C@H:23]1[NH:26][C:25](=[O:27])[C@@H:24]1[O:28][CH3:29].O1CCOCC1.[I-].[Na+]>O.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:23]2[NH:26][C:25](=[O:27])[C@@H:24]2[O:28][CH3:29])=[O:19])=[O:12])=[CH:7][CH:6]=1)([O-:4])=[O:3]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 312751,4-DioxaneHCID 55300418(3S,4R)-4-chloro-3-methoxy-2-oxoazetidineHCID 178523351HCID 178523351, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1061PhosphateSolvent

Procedure

A solution of 350 mg of 4-p-nitrobenzyloxycarbonylaminothiobutyric acid sodium salt in 4 ml of water is added dropwise to a solution of 135 mg of (3S,4R)-4-chloro-3-methoxy-2-oxoazetidine in 6 ml of a phosphate buffer of a pH of 7 and 0.4 ml of dioxan in the presence of 150 mg of sodium iodide.

Sources & evidence

ORD record
ord-d2d51f4908d84fce8d5b449f1c798810
Source dataset
uspto-grants-1990_08
Patent number
US04952690

Reaction notes

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