m-Chloroperbenzoic acid → HCID 20402460, compound

HRID 1980416Notes

Reaction equation

HRID 1980416 reaction equation
[CH:1]([O:14][C:15]([C:17]1[N:18]2[CH:21]([S:22][CH2:23][C:24]=1[C:25]1[S:29][C:28]([C:30]3[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=3)=[N:27][CH:26]=1)[CH:20]([NH:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[C:19]2=[O:44])=[O:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:53])C=1>C(Cl)Cl>[CH:1]([O:14][C:15]([C:17]1[N:18]2[CH:21]([S:22](=[O:53])[CH2:23][C:24]=1[C:25]1[S:29][C:28]([C:30]3[CH:31]=[CH:32][N:33]=[CH:34][CH:35]=3)=[N:27][CH:26]=1)[CH:20]([NH:36][C:37]([O:39][C:40]([CH3:41])([CH3:43])[CH3:42])=[O:38])[C:19]2=[O:44])=[O:16])([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 20402464HCID 20402464, compound

Product 1

HCID 20402460HCID 20402460, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-benzhydryloxycarbonyl-7-t-butoxycarbonylamino-8-oxo-3-[2-(pyridin-4-yl)-thiazol-5-yl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene (24 g) in methylene chloride (370 cc) is oxidised with 85% pure meta-chloroperbenzoic acid (7.92 g) in accordance with the procedure described in Example 2 to give 2-benzhydryloxycarbonyl-7-t-butoxycarbonylamino-8-oxo-3-[2-(pyridin-4-yl)-thiazol-5-yl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene 5-oxide (23 g) in the form of a brown-yellow solid.

Sources & evidence

ORD record
ord-7e05d1d23d4842288b9385ca21d5c301
Source dataset
uspto-grants-1985_04
Patent number
US04508717

Reaction notes

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