Water → Benzyl 2-(3-phenoxyacetamido-4-benzenesulfonylthio-2-azetidinon-1-yl)-3-methyl-3butenoate

HRID 649698Notes

Reaction equation

HRID 649698 reaction equation
[O:1]([CH2:8][C:9]([NH:11][CH:12]1[CH:15](SSC2SC3C=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](=[S:64])([O:52]C2SC3C=CC(OC)=CC=3N=2)=[O:51])[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1.O.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:52][S:50]([C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)(=[O:64])=[O:51])[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:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 2723840Benzenesulfinic acid, sodium saltHCID 14830337Benzyl 2-[3-phenoxyacetamido-4-(5-methoxybenzothiazol-2-yldithio)-2-azetidinon-1-yl]-3-methyl-3-butenoateHCID 538494265-Methoxybenzothiazol-2-yl benzenethiosulfonate

Product 1

HCID 13170072Benzyl 2-(3-phenoxyacetamido-4-benzenesulfonylthio-2-azetidinon-1-yl)-3-methyl-3butenoateYield 96%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A 263 mg quantity of benzyl 2-[3-phenoxyacetamido-4-(5-methoxybenzothiazol-2-yldithio)-2-azetidinon-1-yl]-3-methyl-3-butenoate and 147 mg of 5-methoxybenzothiazol-2-yl benzenethiosulfonate were dissolved in 2.5 ml of acetone. To the solution were added 0.5 ml of water and then 2 mg of sodium benzenesulfinate and the mixture was stirred at room temperature for 3 hour. The precipitated 5-methoxybenzothiazol-2-yl disulfide crystals were filtered and the filtrate was concentrated under reduced pressure. The residue was treated in the same manner as in Example 41, giving benzyl 2-(3-phenoxyacetamido-4-benzenesulfonylthio-2-azetidinon-1-yl)-3-methyl-3-butenoate in a yield of 96%. The NMR spectrum data of the compound were identical with those of the desired compound. Table 2 shows the NMR spectrum data of the compound.

Workup

  1. filtrationThe precipitated 5-methoxybenzothiazol-2-yl disulfide crystals were filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionThe residue was treated in the same manner as in Example 41

Sources & evidence

ORD record
ord-2f400e3c7667452a83b035aa60479885
Source dataset
uspto-grants-1988_04
Patent number
US04740596

Reaction notes

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