m-Chloroperbenzoic acid → HCID 53734017, compound

HRID 1901455Notes

Reaction equation

HRID 1901455 reaction equation
[O:1]=[S@@:2]1[C@@H:7]2[C@H:8]([NH:11][C:12](=[O:20])[CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:9](=[O:10])[N:6]2[C:5]([C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)=[O:22])=[C:4]([O:33][S:34]([C:37]([F:40])([F:39])[F:38])(=[O:36])=[O:35])[CH2:3]1.ClC1C=CC=C(C(OO)=[O:49])C=1>C(Cl)(Cl)Cl>[O:1]=[S:2]1(=[O:49])[C@@H:7]2[C@H:8]([NH:11][C:12](=[O:20])[CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:9](=[O:10])[N:6]2[C:5]([C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)=[O:22])=[C:4]([O:33][S:34]([C:37]([F:39])([F:40])[F:38])(=[O:36])=[O:35])[CH2:3]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 10326269HCID 10326269, compound

Product 1

HCID 53734017HCID 53734017, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of p-methoxybenzyl(1S,6R,7R)-1-oxo-7-phenylacetamido-3-(trifluoro-methanesulphonyloxy)ceph-3-em-4-carboxylate (767 mg, 1.27 mmol) and m-chloroperbenzoic acid (939 mg, 3.81 mmol) in chloroform (60 ml) was heated to reflux. After refluxing for 7 hours the mixture was chromatographed to give the title compound (560 mg, 71%); νmax (KBr) 1819, 1740, 1697 cm-1 ; δH (CDCl3) 3.60 (2H, m), 3.81 (3H, s), 3.87 (1H, d, J 18.1 Hz), 4.17 (1H, d, J 18.1 Hz), 4.53 (1H, d, J 4.9), 5.20 (1H, d, J 11.8 Hz), 5.37 (1H, d, J 11.8 Hz), 6.08 (1H, dd, J 4.9, 9.9 Hz), 6.55 (1H, d, J 9.8 Hz), 6.89 (2H, d, J 8.7 Hz), 7.18-7.37 (7H, m).

Workup

  1. temperaturewas heated to reflux
  2. temperatureAfter refluxing for 7 hours the mixture
  3. customwas chromatographed

Sources & evidence

ORD record
ord-caef04687ea84a40ae48cc540538a0aa
Source dataset
uspto-grants-1996_11
Patent number
US05578592

Reaction notes

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