Dimethyl Sulfide → 7beta-Phenylacetylaminocepham-3-one-4xi-carboxylic acid diphenylmethyl ester

HRID 1995801Notes

Reaction equation

HRID 1995801 reaction equation
[C:1]1([CH:7]([O:14][C:15]([C@@H:17]2[N:22]3[C:23](=[O:35])[C@@H:24]([NH:25][C:26](=[O:34])[CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C@H:21]3[S:20][CH2:19][C:18]2=C)=[O:16])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O=O.[O:39]=[O+][O-].O=[O+][O-].CSC>CO>[C:8]1([CH:7]([O:14][C:15]([CH:17]2[N:22]3[C:23](=[O:35])[C@@H:24]([NH:25][C:26](=[O:34])[CH2:27][C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)[C@H:21]3[S:20][CH2:19][C:18]2=[O:39])=[O:16])[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 1068Dimethyl SulfideHCID 24823OzoneHCID 142776033-Methylene-7beta-phenylacetylamino-cepham-4alpha-carboxylic acid diphenylmethyl esterHCID 131711318Oxygen ozone

Product 1

HCID 98921957beta-Phenylacetylaminocepham-3-one-4xi-carboxylic acid diphenylmethyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
-70 °C

Procedure

A solution of 0.50 g of 3-methylene-7β-phenylacetylamino-cepham-4α-carboxylic acid diphenylmethyl ester in 100 ml of methanol is treated for 6.5 minutes at -70° C. with an oxygen-ozone stream containing 0.175 mmol of ozone/minute. The reaction mixture is mixed with 0.5 ml of dimethyl sulphide and stirred for one hour at -70° C., then for 2 hours at room temperature and evaporated to dryness. The residue, in methylene chloride is chromatographed on 15 g of silica gel. Elution with methylene chloride yields amorphous 7β-phenylacetylaminocepham-3-one-4ξ-carboxylic acid diphenylmethyl ester, thin layer chromatography (silica gel): Rf~0.47 (system: toluene/acetone/methanol/acetic acid, 80:10:5:5); infrared absorption spectrum (in methylene chloride): characteristic bands at 2.95μ, 5.61μ, 5.77μ, 5.85μ, 5.95μ, 6.21μ and 6.87μ; the compound shows a positive reaction with iron-III chloride.

Workup

  1. waitfor 2 hours at room temperature
  2. customevaporated to dryness
  3. customThe residue, in methylene chloride is chromatographed on 15 g of silica gel
  4. washElution with methylene chloride

Sources & evidence

ORD record
ord-3281dd6a2c594fb7af6f43e8b6845528
Source dataset
uspto-grants-1983_09
Patent number
US04405778

Reaction notes

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