m-Chloroperbenzoic acid → Diphenylmethyl 7-(2-thienylacetamido)-3-(1-acetoxyethyl)-3-cephem-4-carboxylate 1-oxide

HRID 596835Notes

Reaction equation

HRID 596835 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:39](=[O:40])[N:12]2[CH:13]([C:23]([O:25][CH:26]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:24])[C:14]([CH:17]([O:19][C:20](=[O:22])[CH3:21])[CH3:18])=[CH:15][S:16][C@H:11]12)=[O:8].ClC1C=CC=C(C(OO)=[O:49])C=1>C(Cl)(Cl)Cl>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:39](=[O:40])[N:12]2[C:13]([C:23]([O:25][CH:26]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[O:24])=[C:14]([CH:17]([O:19][C:20](=[O:22])[CH3:21])[CH3:18])[CH2:15][S:16](=[O:49])[C@H:11]12)=[O:8]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 70617660Benzhydryl 7-(2-thienylacetamido)-3-(1-acetoxyethyl)-2-cephem-4-carboxylate

Product 1

HCID 70617865Diphenylmethyl 7-(2-thienylacetamido)-3-(1-acetoxyethyl)-3-cephem-4-carboxylate 1-oxide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Conditions

Temperature
5 °C

Procedure

To a cooled (5° C.), stirred solution of 0.897 g. of benzhydryl 7-(2-thienylacetamido)-3-(1-acetoxyethyl)-2-cephem-4-carboxylate in 80 ml. of chloroform was added a solution of 0.348 g. of 85 percent m-chloroperbenzoic acid in 3 ml. of chloroform. The reaction mixture was allowed to stir with cooling for 30 minutes after which time it was transferred to a separatory funnel with the aid of additional chloroform and washed successively with sodium bicarbonate solution (2X), and brine (2X) and dried over anhydrous sodium sulfate. The residue obtained by evaporation in vacuo to a froth which was chromatographed on a silica gel column using a toluene-ethyl acetate gradient to give 0.243 g. (26 percent) of what was labeled diastereoisomer I and 0.514 g. (55 percent) of what was labeled diastereoisomer II of the title product; isomer I coming off the column first.

Workup

  1. stirringto stir
  2. temperaturewith cooling for 30 minutes after which time it
  3. washwashed successively with sodium bicarbonate solution (2X), and brine (2X)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe residue obtained by evaporation in vacuo to a froth which
  6. customwas chromatographed on a silica gel column
  7. customto give 0.243 g

Sources & evidence

ORD record
ord-b2bde4495ffd467b9facc12c7713924b
Source dataset
uspto-grants-1977_03
Patent number
US04012380

Reaction notes

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