Methanol → HCID 12492923, compound

HRID 1701811Notes

Reaction equation

HRID 1701811 reaction equation
[Cl-].[Mg+2].[Cl-].[CH3:4][C:5]1([CH3:26])S[C@@H:8]2[C@H:10]([NH:13][C:14]([CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[O:15])[C:11](=[O:12])[N:7]2[C@H:6]1[C:23]([OH:25])=[O:24].[CH3:27]O>C(O)(C)(C)C.[Pt]>[CH3:27][O:25][C:23]([C:6]([N:7]1[C:11](=[O:12])[C@@H:10]2[C@H:8]1[O:15][C:14]([CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[N:13]2)=[C:5]([CH3:26])[CH3:4])=[O:24]

Participants

6

Reactant 3

HCID 887MethanolHCID 5904Penicillin GHCID 5360315Magnesium Chloride

Product 1

HCID 12492923HCID 12492923, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6386tert-ButanolSolvent

Procedure

Magnesium chloride (36 mg) was dissolved in a mixture of 2.5 ml of methanol and 0.5 ml of tertbutyl alcohol. To the solution was added 53 mg of methyl ester of penicillin G to prepare an electrolyte. With platinum electrodes (1 cm2) dipped into the electrolyte, electrolysis was continued for 150 minutes (about 6 F) at a temperature of less than 0° C. and 3 to 8 V by applying constant current of 10 mA. Thereafter, the reaction mixture was stirred for about 30 minutes and extracted with chloroform. The extract was treated in the same manner as in Example 1, giving 41 mg of contemplated compound in 87% yield. The results of instrumental analyses were found identical with those of Example 1.

Workup

  1. customto prepare an electrolyte
  2. customat a temperature of less than 0° C. and 3 to 8 V
  3. extractionextracted with chloroform
  4. additionThe extract was treated in the same manner as in Example 1

Sources & evidence

ORD record
ord-d9b098010566494ab58d51595b0203e0
Source dataset
uspto-grants-1983_04
Patent number
US04379032

Reaction notes

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