Water → HCID 13530978, compound

HRID 649701Notes

Reaction equation

HRID 649701 reaction equation
[O:1]([CH2:8][C:9]([NH:11][CH:12]1[CH:15](SSC2SC3C=C(C)C=CC=3N=2)[N:14]([CH:28]([C:42]([CH3:44])=[CH2:43])[C:29]([O:31][CH2:32][C:33]([C:35]2[CH:40]=[CH:39][C:38]([Br:41])=[CH:37][CH:36]=2)=[O:34])=[O:30])[C:13]1=[O:45])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:46]1([S:52](=[S:65])([O:54]C2SC3C=C(C)C=CC=3N=2)=[O:53])[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=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:54][S:52]([C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)(=[O:65])=[O:53])[N:14]([CH:28]([C:42]([CH3:44])=[CH2:43])[C:29]([O:31][CH2:32][C:33]([C:35]2[CH:40]=[CH:39][C:38]([Br:41])=[CH:37][CH:36]=2)=[O:34])=[O:30])[C:13]1=[O:45])=[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 20141911HCID 20141911, compoundHCID 54314629HCID 54314629, compound

Product 1

HCID 13530978HCID 13530978, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A 1.23 g quantity of p-bromophenacyl 2-[3-phenoxyacetamido-4-(6-methylbenzothiazol-2-yldithio)-2-azetidinon-1-yl]-3-methyl-3-butenoate and 572 mg of 6-methylbenzothiazol-2-yl benzenethiosulfonate were dissolved in 10 ml of acetone. To the solution were added 2 ml of water and then 3 mg of sodium benzenesulfinate. The mixture was stirred at room temperature for 5 hours. The precipitated 6-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 p-bromophenacyl 2-(3-phenoxyacetamido-4-benzenesulfonylthio-2-azetidinon-1-yl)-3-methyl-3-butenoate in a yield of 94%. The NMR spectrum data of the compound thus obtained were identical with those of the desired compound. Table 2 below shows the data thereof.

Workup

  1. filtrationThe precipitated 6-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-d11e6608d3874ddbbf0ac5d1a1e82e78
Source dataset
uspto-grants-1988_04
Patent number
US04740596

Reaction notes

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