m-Chloroperbenzoic acid → Benzhydryl 7-[2-(2-tritylaminothiazol-4-yl)-2-difluoromethoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylate-1-oxide

HRID 34503Notes

Reaction equation

HRID 34503 reaction equation
[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:57][O:58][CH:59]([F:61])[F:60])[C:27]([NH:29][CH:30]2[C:55](=[O:56])[N:32]3[C:33]([C:39]([O:41][CH:42]([C:49]4[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=4)[C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)=[O:40])=[C:34]([CH2:37][Cl:38])[CH2:35][S:36][C@H:31]23)=[O:28])[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:70])C=1.S(=O)(O)[O-].[Na+].C(=O)(O)[O-].[Na+]>O.C(OCC)(=O)C>[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:57][O:58][CH:59]([F:61])[F:60])[C:27]([NH:29][CH:30]2[C:55](=[O:56])[N:32]3[C:33]([C:39]([O:41][CH:42]([C:49]4[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=4)[C:43]4[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=4)=[O:40])=[C:34]([CH2:37][Cl:38])[CH2:35][S:36](=[O:70])[C@H:31]23)=[O:28])[N:25]=1)([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 23665763Sodium BisulfiteHCID 131715668Benzhydryl 7-[2-(2-tritylaminothiazol-4-yl)-2-difluoromethoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylate

Product 1

HCID 131715684Benzhydryl 7-[2-(2-tritylaminothiazol-4-yl)-2-difluoromethoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylate-1-oxideYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of benzhydryl 7-[2-(2-tritylaminothiazol-4-yl)-2-difluoromethoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylate (syn isomer) (35 g), m-chloroperbenzoic acid (8.64 g) and ethyl acetate (300 ml) was stirred for 30 minutes at 0° to 5° C. and then, water (300 ml), sodium bisulfite and sodium bicarbonate were added thereto. The organic layer was separated, washed with an aqueous solution of sodium chloride, dried over magnesium sulfate and evaporated. The residue was triturated with diisopropyl ether to give benzhydryl 7-[2-(2-tritylaminothiazol-4-yl)-2-difluoromethoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylate-1-oxide (syn isomer) (29.93 g).

Workup

  1. customThe organic layer was separated
  2. washwashed with an aqueous solution of sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-93268cfdc70447dbbff9ca9aaf842625
Source dataset
uspto-grants-1988_08
Patent number
US04761410

Reaction notes

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