Methanol → HCID 57130304, compound

HRID 1701813Notes

Reaction equation

HRID 1701813 reaction equation
[Cl-].[Li+].[CH3:3][C:4]1([CH3:26])S[C@@H:7]2[C@H:9]([NH:12][C:13]([CH2:15][O:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[O:14])[C:10](=[O:11])[N:6]2[C@H:5]1[C:23]([OH:25])=[O:24].[CH3:27]O>C(O)(C)(C)C.[Pt]>[CH3:27][O:25][C:23]([C:5]([N:6]1[C:10](=[O:11])[C@@H:9]2[C@H:7]1[O:14][C:13]([CH2:15][O:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[N:12]2)=[C:4]([CH3:26])[CH3:3])=[O:24]

Participants

6

Reactant 3

HCID 887MethanolHCID 6869Penicillin VHCID 433294Lithium Chloride

Product 1

HCID 57130304HCID 57130304, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6386tert-ButanolSolvent

Procedure

Lithium chloride (6.7 mg) was dissolved in a mixture of 2 ml of methanol and 0.5 ml of tert-butyl alcohol. Thereto was added 72 mg of methyl ester of penicillin V to prepare an electrolyte. Electrolysis was performed at a temperature of less than -70° C. and 10 to 15 V for 160 minutes (5 F) by dipping platinum electrodes (1 cm2) in the electrolyte and passing constant current of 10 mA through the electrolyte. Thereafter, the reaction mixture was stirred at less than -10° C. for about 30 minutes and extracted with ethyl acetate. The extract was treated in the same manner as in Example 1, affording 53 mg of contemplated compound in 80% yield.

Workup

  1. customto prepare an electrolyte
  2. extractionextracted with ethyl acetate
  3. additionThe extract was treated in the same manner as in Example 1

Sources & evidence

ORD record
ord-09e6e0ec5c384307baafe870dbfe0f4a
Source dataset
uspto-grants-1983_04
Patent number
US04379032

Reaction notes

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