m-Chloroperbenzoic acid → Benzhydryl 7-[2-t-butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetamido]-3-(1,2,4-triazolo[4,3-b]pyridazin-6-yl)thiomethyl-3-cephem-4-carboxylate-1-oxide

HRID 615413Notes

Reaction equation

HRID 615413 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[C:12]([O:16][C:17]([CH2:19][O:20][N:21]=[C:22]([C:62]1[N:63]=[CH:64][S:65][CH:66]=1)[C:23]([NH:25][CH:26]1[C:60](=[O:61])[N:28]2[C:29]([C:44]([O:46][CH:47]([C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)[C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)=[O:45])=[C:30]([CH2:33][S:34][C:35]3[CH:36]=[CH:37][C:38]4[N:39]([CH:41]=[N:42][N:43]=4)[N:40]=3)[CH2:31][S:32][C@H:27]12)=[O:24])=[O:18])([CH3:15])([CH3:14])[CH3:13].C(OC(CON=C(C1N=CSC=1)C(NC1C(=O)N2C(C(OC(C3C=CC=CC=3)C3C=CC=CC=3)=O)C(CSC3C=CC4N(C=NN=4)N=3)=CS[C@H]12)=O)=O)(C)(C)C>C(OCC)(=O)C>[C:12]([O:16][C:17]([CH2:19][O:20][N:21]=[C:22]([C:62]1[N:63]=[CH:64][S:65][CH:66]=1)[C:23]([NH:25][CH:26]1[C:60](=[O:61])[N:28]2[C:29]([C:44]([O:46][CH:47]([C:54]3[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=3)[C:48]3[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=3)=[O:45])=[C:30]([CH2:33][S:34][C:35]3[CH:36]=[CH:37][C:38]4[N:39]([CH:41]=[N:42][N:43]=4)[N:40]=3)[CH2:31][S:32](=[O:9])[C@H:27]12)=[O:24])=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 131714105Benzhydryl 7-[2-t-butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetamido]-3-(1,2,4-triazolo[4,3-b]pyridazin-6-yl)thiomethyl-3-cephem-4-carboxylateHCID 131714106Benzhydryl 7-[2-t-butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetamido]-3-(1,2,4-triazolo[4,3-b]pyridazin-6-yl)thiomethyl-2-cephem-4-carboxylate

Product 1

HCID 131714104Benzhydryl 7-[2-t-butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetamido]-3-(1,2,4-triazolo[4,3-b]pyridazin-6-yl)thiomethyl-3-cephem-4-carboxylate-1-oxideYield 91%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of m-chloroperbenzoic acid (0.4 g) (purity: 80%) in ethyl acetate (5 ml) was added to a solution of a mixture (1.4 g) of benzhydryl 7-[2-t-butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetamido]-3-(1,2,4-triazolo[4,3-b]pyridazin-6-yl)thiomethyl-3-cephem-4-carboxylate (syn isomer) and benzhydryl 7-[2-t-butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetamido]-3-(1,2,4-triazolo[4,3-b]pyridazin-6-yl)thiomethyl-2-cephem-4-carboxylate (syn isomer) in ethyl acetate (10 ml) under ice-cooling and the resultant mixture was stirred for 1 hour at the same temperature. The resulting solution was washed with a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride, successively. The organic layer was dried over magnesium sulfate and evaporated to give benzhydryl 7-[2-t-butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetamido]-3-(1,2,4-triazolo[4,3-b]pyridazin-6-yl)thiomethyl-3-cephem-4-carboxylate-1-oxide (syn isomer) (1.3 g).

Workup

  1. temperaturecooling
  2. washThe resulting solution was washed with a saturated aqueous solution of sodium bicarbonate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-cf62f555e50f44d9948a7609d206261c
Source dataset
uspto-grants-1985_02
Patent number
US04499088

Reaction notes

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