m-Chloroperbenzoic acid → HCID 67908185, compound

HRID 467366Notes

Reaction equation

HRID 467366 reaction equation
[CH3:1][C:2]1[O:7][C:6](=[O:8])[CH:5]=[C:4]([S:9][C:10]2[CH2:11][S:12][C@@H:13]3[C@H:33]([NH:34][C:35](=[O:43])[CH2:36][C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[C:32](=[O:44])[N:14]3[C:15]=2[C:16]([O:18][CH:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[CH:3]=1.CC1[O:51]C(=O)C=C(SC2C(C(OC(C3C=CC=CC=3)C3C=CC=CC=3)=O)N3C(=O)[C@@H](NC(=O)CC4C=CC=CC=4)[C@H]3SC=2)C=1.ClC1C=CC=C(C(OO)=O)C=1>ClCCl>[CH3:1][C:2]1[O:7][C:6](=[O:8])[CH:5]=[C:4]([S:9][C:10]2[CH2:11][S:12](=[O:51])[C@@H:13]3[C@H:33]([NH:34][C:35](=[O:43])[CH2:36][C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=4)[C:32](=[O:44])[N:14]3[C:15]=2[C:16]([O:18][CH:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[O:17])[CH:3]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 67908162HCID 67908162, compoundHCID 67908479HCID 67908479, compound

Product 1

HCID 67908185HCID 67908185, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A stirred solution of diphenylmethyl 3-(6-methyl-2-oxo-2H-pyran-4-ylthio) -7β-phenylacetamidoceph-3-em-4-carboxylate and diphenylmethyl 3-(6-methyl-2-oxo-2H-pyran-4-ylthio) -7β-phenylacetamidoceph-2-em-4-carboxylate (763 mg) in dichloromethane (10 ml) was cooled in an ice bath, and a solution of m-chloroperbenzoic acid (211 mg of 85%) in dichloromethane (5 ml) was added. The mixture was stirred at 0° for 40 mins. and then washed with sodium bicarbonate solution, sodium metabisulphite solution, water and brine. The solution was dried over magnesium sulphate and evaporated. The title compound (581 mg) was isolated by column chromatography of the residue using gradient elution (Kieselgel 1:1 hexane:ethyl acetate going to neat ethyl acetate). υmax (CHCl3) 3390, 1805, 1720 cm-1, δH (CDCl3) 2.14 (3H, s) 3.36 (1H, d, J 18.1Hz), 3.60 (2H, s), 3.75 (1H, d, J 18.2Hz), 4.51 (1H, d, J 4.8Hz), 5.72 (1H, s), 5.95 (1H, s) 6.13 (1H, dd, J 4.8 and 9.7Hz), 6.94 (1H, d, J 9.7Hz), 6.97 (1H, s), 7.2-7.4 (15H, m).

Workup

  1. washand then washed with sodium bicarbonate solution, sodium metabisulphite solution, water and brine
  2. dry with materialThe solution was dried over magnesium sulphate
  3. customevaporated

Sources & evidence

ORD record
ord-497b11d4a614407eb5f6f26453ad3693
Source dataset
uspto-grants-1992_10
Patent number
US05158946

Reaction notes

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