Water → 3,4,5-Trimethoxy-2,6 dichlorobenzyl 2-(3-phenoxyacetamido-4-benzenesulfonylthio-2-azetidinon-1-yl)-3-methyl-3-butenoate

HRID 649700Notes

Reaction equation

HRID 649700 reaction equation
[O:1]([CH2:8][C:9]([NH:11][CH:12]1[CH:15]([S:16]SC2SC3C=CC=C(C)C=3N=2)[N:14]([CH:28]([C:47]([CH3:49])=[CH2:48])[C:29]([O:31][CH2:32][C:33]2[C:38]([Cl:39])=[C:37]([O:40][CH3:41])[C:36]([O:42][CH3:43])=[C:35]([O:44][CH3:45])[C:34]=2[Cl:46])=[O:30])[C:13]1=[O:50])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:51]1([S:57](=S)([O:59]C2SC3C=CC=C(C)C=3N=2)=[O:58])[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=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:16][S:57]([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)(=[O:59])=[O:58])[N:14]([CH:28]([C:47]([CH3:49])=[CH2:48])[C:29]([O:31][CH2:32][C:33]2[C:34]([Cl:46])=[C:35]([O:44][CH3:45])[C:36]([O:42][CH3:43])=[C:37]([O:40][CH3:41])[C:38]=2[Cl:39])=[O:30])[C:13]1=[O:50])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 2723840Benzenesulfinic acid, sodium saltHCID 201419153,4,5-Trimethoxy-2,6-dichlorobenzyl 2-[3-phenoxyacetamido-4-(4-methylbenzothiazol-2-yldithio)-2-azetidinon-1-yl]-3-methyl-3-butenoateHCID 543594404-Methylbenzothiazol-2-yl benzenethiosulfonate

Product 1

HCID 135309753,4,5-Trimethoxy-2,6 dichlorobenzyl 2-(3-phenoxyacetamido-4-benzenesulfonylthio-2-azetidinon-1-yl)-3-methyl-3-butenoateYield 86%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A 1.03 g quantity of 3,4,5-trimethoxy-2,6-dichlorobenzyl 2-[3-phenoxyacetamido-4-(4-methylbenzothiazol-2-yldithio)-2-azetidinon-1-yl]-3-methyl-3-butenoate and 448 mg of 4-methylbenzothiazol-2-yl benzenethiosulfonate were dissolved in 10 ml of acetone. To the solution were added 2 ml of water and then 8 mg of sodium benzenesulfinate. The mixture was stirred at room temperature for 5 hours. The precipitated 4-methylbenzothiazol-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 3,4,5-trimethoxy-2,6-dichlorobenzyl 2-(3-phenoxyacetamido-4-benzenesulfonylthio-2-azetidinon-1-yl)-3-methyl-3-butenoate in a yield of 86%. The NMR spectrum data of the compound thus obtained were identical with those of the desired compound. Table 2 below indicates the data thereof.

Workup

  1. filtrationThe precipitated 4-methylbenzothiazol-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-cea30d9eaac94661921a7e5a18098607
Source dataset
uspto-grants-1988_04
Patent number
US04740596

Reaction notes

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