m-Chloroperbenzoic acid → HCID 10326269, compound

HRID 1901454Notes

Reaction equation

HRID 1901454 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][C@@H:11]2[C:38](=[O:39])[N:13]3[C:14]([C:26]([O:28][CH2:29][C:30]4[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=4)=[O:27])=[C:15]([O:18][S:19]([C:22]([F:25])([F:24])[F:23])(=[O:21])=[O:20])[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1C=CC=C(C(OO)=[O:48])C=1>ClCCl>[O:48]=[S@@:17]1[C@@H:12]2[C@H:11]([NH:10][C:8](=[O:9])[CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:38](=[O:39])[N:13]2[C:14]([C:26]([O:28][CH2:29][C:30]2[CH:31]=[CH:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=2)=[O:27])=[C:15]([O:18][S:19]([C:22]([F:24])([F:25])[F:23])(=[O:21])=[O:20])[CH2:16]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 10769651HCID 10769651, compound

Product 1

HCID 10326269HCID 10326269, compoundYield 75.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of p-methoxybenzyl (6R,7R)-7-phenylacetamido-3-(trifluoromethanesulphonyloxy)ceph-3-em-4-carboxylate (1.0 g, 1.7 mmol) in dichloromethane (25 ml) was treated with a solution of m-chloroperbenzoic acid (70%) (0.45, 1.8 mmol) in dichloromethane (15 ml). After stirring at room temperature for 30 min the solvent was evaporated and the residue crystallised from dichloro-methane/hexane to give the title compound (775 mg, 75%); m/z (3-NOBA sodium) 625 (MNa+); νmax (KBr) 1793, 1736, 1649 cm-1 ; δH (CDCl3) 3.47 (1H, dd, J 18.4, 1.4 Hz), 3.63 (1H, d, J 15.6 Hz), 3.66 (1H, d, J 15.6 Hz), 3.81 (3H, s), 3.87 (1H, d, J 18.4 Hz), 4.53 (1H, dd, J 4.8, 1.4 Hz), 5.20 (1H, d, J 11.7 Hz), 5.36 (1H, d, J 11.7 Hz), 6.07 (1H, dd, J 4.9, 9.8 Hz), 6.75 (1H, d, J 9.8 Hz), 6.89 (2H, d, J 8.6 Hz), 7.25-7.36 (7H, m).

Workup

  1. customwas evaporated
  2. customthe residue crystallised from dichloro-methane/hexane

Sources & evidence

ORD record
ord-3441dbdd39d5413592e04e4f450219d0
Source dataset
uspto-grants-1996_11
Patent number
US05578592

Reaction notes

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