4-Nitrobenzenesulfonyl chloride → HCID 10500592, compound

HRID 484031Notes

Reaction equation

HRID 484031 reaction equation
N1(C2CCCCCCCCCC2)CCCCCCCCCN1.[CH2:23]([O:30][C:31]([CH:33]1[NH:36][C:35](=[O:37])[CH2:34]1)=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[N+:38]([C:41]1[CH:46]=[CH:45][C:44]([S:47](Cl)(=[O:49])=[O:48])=[CH:43][CH:42]=1)([O-:40])=[O:39]>C(Cl)Cl>[N+:38]([C:41]1[CH:42]=[CH:43][C:44]([S:47]([N:36]2[CH:33]([C:31]([O:30][CH2:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)=[O:32])[CH2:34][C:35]2=[O:37])(=[O:49])=[O:48])=[CH:45][CH:46]=1)([O-:40])=[O:39]

Participants

5

Reactant 3

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 2808534benzyl 4-oxoazetidine-2-carboxylateHCID 57346892Diazabicycloundecane

Product 1

HCID 10500592HCID 10500592, compoundYield 20.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diazabicycloundecane (152 mg, 1 mM) was added to a mixture of 205 mg (1 mM) 4-benzyloxycarbonyl azetidin-2-one and 181 mg (1 mM) p-nitrobenzenesulfonyl chloride in 10 ml methylene chloride at room temperature. After stirring 21/2 hours, the orange solution was washed with water, dried over MgSO4, and concentrated in vacuo. The residue was chromatographed on silica gel in hexane/ethyl acetate to yield 64 mg (17%) of 1-p-nitrophenylsulfonyl-4-benzyloxycarbonyl azetidin-2-one.

Workup

  1. washthe orange solution was washed with water
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was chromatographed on silica gel in hexane/ethyl acetate

Sources & evidence

ORD record
ord-8febbc4900ea4e69bf957db13ec007c3
Source dataset
uspto-grants-1993_07
Patent number
US05229381

Reaction notes

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