Dimethyl Sulfoxide → HCID 70524504, compound

HRID 1902513Notes

Reaction equation

HRID 1902513 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:32](=[O:33])[N:13]3[CH:14]([C:19]([O:21][CH2:22][C:23]4[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=4)=[O:20])[CH:15](O)[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CS(C)=O.[C:38]([O:41][C:42](=O)C)(=[O:40])[CH3:39].O>C(OCC)(=O)C>[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:32](=[O:33])[N:13]3[CH:14]([C:19]([O:21][CH2:22][C:23]4[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=4)=[O:20])[C:15](=[CH:42][O:41][C:38](=[O:40])[CH3:39])[CH2:16][S:17][C@H:12]23)=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 7918Acetic AnhydrideHCID 70523160HCID 70523160, compound

Product 1

HCID 70524504HCID 70524504, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-Nitrobenzyl 7-(2-phenylacetamido)-3-hydroxycepham-4-carboxylate (1.5 g.) was added to a solution of dimethylsulfoxide (15 ml.) and acetic anhydride (15 ml.), and stirred at room temperature for 5 hours. After adding the resultant mixture into water, ethyl acetate was added to the solution, adjusted to pH 7.5 and stirred for an hour. The ethyl acetate layer was separated, washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was subjected to column chromatography on silica gel with a solution of diisopropyl ether and ethyl acetate (5:1) to give 4-nitrobenzyl 7-(2-phenylacetamido)-3-acetoxymethylenecepham-4-carboxylate (660 mg.).

Workup

  1. additionwas added to the solution
  2. stirringstirred for an hour
  3. customThe ethyl acetate layer was separated
  4. washwashed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. concentrationThe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c9d5d2784cde43308be2fa4800aae2d1
Source dataset
uspto-grants-1982_12
Patent number
US04363807

Reaction notes

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