Diazomethane → HCID 15702727, compound

HRID 436033Notes

Reaction equation

HRID 436033 reaction equation
[C:1]([CH:4]([N:8]1[CH:11]([S:12][N:13]2[C:17](=[O:18])[C:16]3=[CH:19][CH:20]=[CH:21][CH:22]=[C:15]3[C:14]2=[O:23])[CH:10]([NH:24][C:25](=[O:33])[CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:9]1=[O:34])[C:5]([CH3:7])=[CH2:6])([OH:3])=[O:2].[N+](=[CH2:37])=[N-]>C(OCC)C>[CH3:37][O:2][C:1]([CH:4]([N:8]1[CH:11]([S:12][N:13]2[C:14](=[O:23])[C:15]3=[CH:22][CH:21]=[CH:20][CH:19]=[C:16]3[C:17]2=[O:18])[CH:10]([NH:24][C:25](=[O:33])[CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:9]1=[O:34])[C:5]([CH3:7])=[CH2:6])=[O:3]

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 54366830HCID 54366830, compound

Product 1

HCID 15702727HCID 15702727, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

14 g (purity 70%; 20 mmoles) of 1-(1-carboxy-2-methylprop-2-enyl)-3-phenylacetamido-4-phthalimidothio-azetidin-2-one was treated with a diazomethane solution in diethyl ether. After evaporation of the reaction mixture to dryness, benzene was added. After filtering off the phthalimide, the filtrate was concentrated and chromatographed [silica gel; toluene - ethyl acetate 4:1(v/v] to obtain 6.24 g (62% yield) of 1-(1-methoxycarbonyl-2-methylprop-2-enyl)-3-phenylacetamido-4-phthalimidothio-azetidin-2-one.

Workup

  1. customAfter evaporation of the reaction mixture to dryness, benzene
  2. additionwas added
  3. filtrationAfter filtering off the phthalimide
  4. concentrationthe filtrate was concentrated
  5. customchromatographed [silica gel; toluene - ethyl acetate 4:1(v/v]

Sources & evidence

ORD record
ord-21e63034f33848b8aedf7ffbb9e243ee
Source dataset
uspto-grants-1977_02
Patent number
US04007202

Reaction notes

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