HCID 86740397, compound → HCID 86740422, compound

HRID 621011Notes

Reaction equation

ClCC([NH:5][C:6]1[S:7][CH:8]=[C:9]([C:11](=[N:30][O:31][CH3:32])[C:12]([NH:14][C@H:15]2[C@H:18]([S:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])[N:17]([S:25]([O-:28])(=[O:27])=[O:26])[C:16]2=[O:29])=[O:13])[N:10]=1)=O.[Na+:33].CSC(=S)N.[Na]>>[NH2:5][C:6]1[S:7][CH:8]=[C:9]([C:11](=[N:30][O:31][CH3:32])[C:12]([NH:14][C@H:15]2[C@H:18]([S:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])[N:17]([S:25]([O-:28])(=[O:27])=[O:26])[C:16]2=[O:29])=[O:13])[N:10]=1.[Na+:33]

Participants

Reactant 2

HCID 86740397HCID 86740397, compound

HCID 86740423HCID 86740423, compound

Product 1

HCID 86740422HCID 86740422, compoundYield 51%

Procedure

To a solution of 0.273 g of sodium (3R,4S)-3-[2-(2-chloroacetamidothiazol-4-yl)-2-methoxyiminoacetamido]-4-methoxycarbonylmethylthio-2-oxoazetidine-1-sulfonate in 6 ml of a buffer solution (pH 6.86) is added 67.8 mg of sodium monomethyldithiocarbamate under ice-cooling. After stirring for 2 hours at room temperature, the reaction mixture is purified in the same procedure as in Example 3B to give 0.120 g of sodium (3R,4S)-3-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-4-methoxycarbonylmethylthio-2-oxoazetidine-1-sulfonate.

Workup

temperaturecooling
customthe reaction mixture is purified in the same procedure as in Example 3B

Sources & evidence

ORD record: ord-fc2486cf5aeb453785cff72bed337c40
Source dataset: uspto-grants-1989_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04822790

Reaction notes

Loading…