Benzenesulfinic acid, sodium salt → Benzyl 2-(3-phenoxyacetamido-4-benzenesulfonylthio-2-azetidinon-1-yl)-3-methyl-3butenoate

HRID 986486Notes

Reaction equation

HRID 986486 reaction equation
[O:1]([CH2:8][C:9]([NH:11][CH:12]1[CH:15]([S:16]SC2SC3C=CC(OC)=CC=3N=2)[N:14]([CH:29]([C:40]([CH3:42])=[CH2:41])[C:30]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:31])[C:13]1=[O:43])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:44]1([S:50](C#N)(=[O:52])=[O:51])[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1.C1(S([O-])=O)C=CC=CC=1.[Na+]>CC(C)=O>[O:1]([CH2:8][C:9]([NH:11][CH:12]1[CH:15]([S:16][S:50]([C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)(=[O:51])=[O:52])[N:14]([CH:29]([C:40]([CH3:42])=[CH2:41])[C:30]([O:32][CH2:33][C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)=[O:31])[C:13]1=[O:43])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 2723840Benzenesulfinic acid, sodium saltHCID 10313279Benzenesulfonyl cyanideHCID 14830337Benzyl 2-[3-phenoxyacetamido-4-(5-methoxybenzothiazol-2-yldithio)-2-azetidinon-1-yl]-3-methyl-3-butenoate

Product 1

HCID 13170072Benzyl 2-(3-phenoxyacetamido-4-benzenesulfonylthio-2-azetidinon-1-yl)-3-methyl-3butenoateYield 93%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A 250 mg quantity of benzyl 2-[3-phenoxyacetamido-4-(5-methoxybenzothiazol-2-yldithio)-2-azetidinon-1-yl]-3-methyl-3-butenoate and 79 mg of benzenesulfonyl cyanide were dissolved in 2.5 ml of acetone. To the solution was added 3 mg of sodium benzenesulfinate and the mixture was reacted at room temperature for 2 hours. The same subsequent procedure as in Example 5 was followed, producing benzyl 2-(3-phenoxyacetamido-4-benzenesulfonylthio-2-azetidinon-1-yl)-3-methyl-3butenoate in a yield of 93%. The NMR spectrum data of the compound thus obtained were identical with those of the desired compound. Table 2 below shows the NMR spectrum data thereof.

Workup

  1. customthe mixture was reacted at room temperature for 2 hours

Sources & evidence

ORD record
ord-4b54cb234eee4da3b069a0e0ef2a2874
Source dataset
uspto-grants-1987_12
Patent number
US04713452

Reaction notes

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