m-Chloroperbenzoic acid → HCID 141551045, compound

HRID 1252310Notes

Reaction equation

HRID 1252310 reaction equation
[CH2:1]([O:3]/[N:4]=[C:5](/[C:36]1[N:37]=[C:38]([NH:41][C:42]([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[S:39][CH:40]=1)\[C:6]([NH:8][CH:9]1[C:34](=[O:35])[N:11]2[C:12]([C:18]([O:20][CH:21]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:19])=[C:13]([CH2:16][Cl:17])[CH2:14][S:15][C@H:10]12)=[O:7])[CH3:2].ClC1C=CC=C(C(OO)=[O:69])C=1>C1C=CC=CC=1>[CH2:1]([O:3]/[N:4]=[C:5](/[C:36]1[N:37]=[C:38]([NH:41][C:42]([C:49]2[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=2)([C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[S:39][CH:40]=1)\[C:6]([NH:8][CH:9]1[C:34](=[O:35])[N:11]2[C:12]([C:18]([O:20][CH:21]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[O:19])=[C:13]([CH2:16][Cl:17])[CH2:14][S:15](=[O:69])[C@H:10]12)=[O:7])[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 88521895HCID 88521895, compound

Product 1

HCID 141551045HCID 141551045, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

4.0 g (4.7 mmol) of benzhydryl 7-[(Z)-2-ethoxyimino-2-(2-tritylaminothiazol-4-yl)acetamido]-3-chloromethyl-3-cephem-4-carboxylate was dissolved in 40 ml of benzene, and 1.0 g (5.8 mmol) of m-chloroperbenzoic acid was added under cooling with ice. The mixture was stirred at room temperature for 40 minutes. The reaction solution was poured into ice water, and extracted with ethyl acetate. The extract solution was washed with a 5% acid sodium bisulfite aqueous solution and with a saturated sodium chloride aqueous solution, then dried over anhydrous sodium sulfate and concentrated under reduced pressure. The oily residue was solidified by an addition of n-hexane, collected by filtration and dried to obtain 3.8 g (yield: 93%) of a powder of the above identified compound.

Workup

  1. temperatureunder cooling with ice
  2. extractionextracted with ethyl acetate
  3. washThe extract solution was washed with a 5% acid sodium bisulfite aqueous solution and with a saturated sodium chloride aqueous solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionThe oily residue was solidified by an addition of n-hexane
  7. filtrationcollected by filtration
  8. customdried

Sources & evidence

ORD record
ord-e5ee3938e11a4d349d0842b6cdb5a714
Source dataset
uspto-grants-1988_05
Patent number
US04742053

Reaction notes

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