Dichloromethane → HCID 70638720, compound

HRID 462319Notes

Reaction equation

HRID 462319 reaction equation
[C:1]([NH:4][CH:5]1[C:30](=[O:31])[N:7]2[C:8]([C:14]([O:16][CH:17]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:15])=[C:9]([CH2:12][OH:13])[CH2:10][S:11][C@H:6]12)(=[O:3])[CH3:2].C(Cl)Cl.ClC1C=CC=C(C(OO)=[O:43])C=1>C(O)(C)C>[C:1]([NH:4][CH:5]1[C:30](=[O:31])[N:7]2[C:8]([C:14]([O:16][CH:17]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[O:15])=[C:9]([CH2:12][OH:13])[CH2:10][S:11](=[O:43])[C@H:6]12)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 70297m-Chloroperbenzoic acidHCID 70638849HCID 70638849, compound

Product 1

HCID 70638720HCID 70638720, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

To a stirred, cooled (0°-5° C.) solution of 876 mg. of benzhydryl 7-acetamido-3-hydroxymethyl-3-cephem-4-carboxylate in a mixture of 40 ml. of methylene chloride and 20 ml. of isopropanol there was added dropwise 407 mg. (equivalent, about 85% pure) of m-chloroperbenzoic acid in 20 ml. of isopropanol, During the addition a precipitate was formed which was collected and washed with ethyl acetate yielding 800 mg. of the titled compound, m.p. 178°-179° C. The NMR, IR, and UV spectra were consistent with the assigned structure.

Workup

  1. temperatureTo a stirred, cooled (0°-5° C.) solution of 876 mg
  2. customwas formed which
  3. customwas collected
  4. washwashed with ethyl acetate yielding 800 mg

Sources & evidence

ORD record
ord-92debd02a5bb4eefacb9e0934a41cffb
Source dataset
uspto-grants-1977_12
Patent number
US04065620

Reaction notes

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