Diazomethane → HCID 86733532, compound

HRID 436030Notes

Reaction equation

HRID 436030 reaction equation
[C:1]([CH:4]([N:8]1[CH:11]([S:12][N:13]2[C:17](=[O:18])[CH2:16][CH2:15][C:14]2=[O:19])[CH:10]([NH:20][C:21](=[O:29])[CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:9]1=[O:30])[C:5]([CH3:7])=[CH2:6])([OH:3])=[O:2].[N+](=[CH2:33])=[N-]>C(OCC)C>[CH3:33][O:2][C:1]([CH:4]([N:8]1[CH:11]([S:12][N:13]2[C:14](=[O:19])[CH2:15][CH2:16][C:17]2=[O:18])[CH:10]([NH:20][C:21](=[O:29])[CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:9]1=[O:30])[C:5]([CH3:7])=[CH2:6])=[O:3]

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 21530757HCID 21530757, compound

Product 1

HCID 86733532HCID 86733532, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1-(1-carboxy-2-methylprop-2-enyl)-3-phenylacetamido-4-succinimidothio-azetidin-2-one was treated with a diazomethane solution in diethyl ether and after evaporation of the reaction mixture to dryness, the residue was purified by column chromatography on silica gel using a 5:3 (v/v) mixture of toluene and ethyl acetate, and finally only ethyl acetate, as an eluent. The structure of 1-(1-methoxycarbonyl-2-methylprop-2-enyl)-3-phenylacetamido-4-succinimidothio-azetidin-2-one so obtained was confirmed by mass-spectrometry and PMR and IR spectroscopy.

Workup

  1. customafter evaporation of the reaction mixture to dryness
  2. customthe residue was purified by column chromatography on silica gel using
  3. additiona 5:3 (v/v) mixture of toluene and ethyl acetate, and finally only ethyl acetate

Sources & evidence

ORD record
ord-6b74342cf866411087d0c351327682dd
Source dataset
uspto-grants-1977_02
Patent number
US04007202

Reaction notes

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