m-Chloroperbenzoic acid → 2-n-Octyloxy-1-n-octyloxymethylethyl 7-[2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate-1-oxide

HRID 1632754Notes

Reaction equation

HRID 1632754 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH:12]([NH:14][C:15]1[S:16][CH:17]=[C:18]([C:20](=[N:57][O:58][CH3:59])[C:21]([NH:23][CH:24]2[C:55](=[O:56])[N:26]3[CH:27]([C:31]([O:33][CH:34]([CH2:45][O:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])[CH2:35][O:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])=[O:32])[CH:28]=[CH:29][S:30][C@H:25]23)=[O:22])[N:19]=1)=[O:13]>C(Cl)Cl>[CH:12]([NH:14][C:15]1[S:16][CH:17]=[C:18]([C:20](=[N:57][O:58][CH3:59])[C:21]([NH:23][CH:24]2[C:55](=[O:56])[N:26]3[C:27]([C:31]([O:33][CH:34]([CH2:35][O:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[CH2:45][O:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])=[O:32])=[CH:28][CH2:29][S:30](=[O:9])[C@H:25]23)=[O:22])[N:19]=1)=[O:13]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 1317139162-n-Octyloxy-1-n-octyloxymethylethyl 7-[2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetamido]-2-cephem-4-carboxylate

Product 1

HCID 1317139182-n-Octyloxy-1-n-octyloxymethylethyl 7-[2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate-1-oxideYield 79.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 3-chloroperbenzoic acid (0.9 g) in methylene chloride (10 ml) was dropwise added to a stirred solution of 2-n-octyloxy-1-n-octyloxymethylethyl 7-[2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetamido]-2-cephem-4-carboxylate (syn isomer, 3.0 g) in methylene chloride (30 ml) at -7° to -3° C. over 30 minutes, and then stirred at 0° C. for 35 minutes. The resultant mixture was washed with a diluted aqueous solution of sodium bicarbonate and saturated aqueous solution of sodium chloride in turn, and dried over anhydrous magnesium sulfate. After removing the solvent from the solution in vacuo, the residue was subjected to column chromatography on silica gel (120 g) with a mixture of chloroform and methanol (20:1). The eluate was evaporated in vacuo to give powder [2.44 g] of 2-n-octyloxy-1-n-octyloxymethylethyl 7-[2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate-1-oxide (syn isomer).

Workup

  1. washThe resultant mixture was washed with a diluted aqueous solution of sodium bicarbonate and saturated aqueous solution of sodium chloride in turn
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customAfter removing the solvent from the solution in vacuo
  4. additionthe residue was subjected to column chromatography on silica gel (120 g) with a mixture of chloroform and methanol (20:1)
  5. customThe eluate was evaporated in vacuo

Sources & evidence

ORD record
ord-be103d50a0654aab89f8c678d03104ab
Source dataset
uspto-grants-1984_10
Patent number
US04477447

Reaction notes

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