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

HRID 649699Notes

Reaction equation

HRID 649699 reaction equation
[O:1]([CH2:8][C:9]([NH:11][CH:12]1[CH:15](SSC2SC3C=C([N+]([O-])=O)C=CC=3N=2)[N:14]([CH:30]([C:41]([CH3:43])=[CH2:42])[C:31]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[O:32])[C:13]1=[O:44])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:45]1([S:51](=[S:66])([O:53]C2SC3C=C([N+]([O-])=O)C=CC=3N=2)=[O:52])[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=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:53][S:51]([C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=2)(=[O:66])=[O:52])[N:14]([CH:30]([C:41]([CH3:43])=[CH2:42])[C:31]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[O:32])[C:13]1=[O:44])=[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 20141913Benzyl 2-[3-phenoxyacetamido-4-(6-nitrobenzothiazol-2-yldithio)-2-azetidinon-1-yl]-3-methyl-3-butenoateHCID 537219196-Nitrobenzothiazol-2-yl benzenethiosulfonate

Product 1

HCID 13170072Benzyl 2-(3-phenoxyacetamido-4-benzenesulfonylthio-2-azetidinon-1-yl)-3-methyl-3butenoateYield 79%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A 198 mg quantity of benzyl 2-[3-phenoxyacetamido-4-(6-nitrobenzothiazol-2-yldithio)-2-azetidinon-1-yl]-3-methyl-3-butenoate and 113 mg of 6-nitrobenzothiazol-2-yl benzenethiosulfonate were dissolved in 2.5 ml of acetone. To the solution were added 0.5 ml of water and then 3 mg of sodium benzenesulfinate. The mixture was stirred at room temperature for 8 hours. The precipitated 6-nitrobenzothiazol-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 1, giving benzyl 2-(3-phenoxyacetamido-4-benzenesulfonylthio-2-azetidinon-1-yl)-3-methyl-3-butenoate in a yield of 79%. The NMR spectrum data of the compound thus obtained were identical with those of the compound produced in Example 3.

Workup

  1. filtrationThe precipitated 6-nitrobenzothiazol-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 1

Sources & evidence

ORD record
ord-0dc4399d564c4773b8ae33a8fc765269
Source dataset
uspto-grants-1988_04
Patent number
US04740596

Reaction notes

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