Acetonitrile → Methyl Acetate

HRID 1580509Notes

Reaction equation

HRID 1580509 reaction equation
[C:1]1([CH:7]([O:14][C:15]([CH:17]2[N:22]3[C:23](=[O:35])[C@@H:24]([NH:25][C:26](=[O:34])[CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C@H:21]3[S:20][CH:19]=[C:18]2[CH2:36][C:37]2[O:41][C:40]([C:42]([O:44][CH:45]([C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)[C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)=[O:43])=[CH:39][CH:38]=2)=[O:16])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(#N)C.ClC1C=CC=C(C(OO)=[O:69])C=1>C(O)(C)C>[C:15]([O:14][CH3:7])(=[O:16])[CH3:17].[C:1]1([CH:7]([O:14][C:15]([C:17]2[N:22]3[C:23](=[O:35])[C@@H:24]([NH:25][C:26](=[O:34])[CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C@H:21]3[S:20](=[O:69])[CH2:19][C:18]=2[CH2:36][C:37]2[O:41][C:40]([C:42]([O:44][CH:45]([C:52]3[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=3)[C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)=[O:43])=[CH:39][CH:38]=2)=[O:16])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 70297m-Chloroperbenzoic acidHCID 131709951HCID 131709951, compound

Product 2

HCID 6584Methyl AcetateHCID 68133867HCID 68133867, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 2.5 g of 3-(5-diphenylmethoxycarbonylfurfuryl)-7β-phenylacetylamino-ceph-2-em-4ξ-carboxylic acid diphenylmethyl ester in 10 ml of a 1:1-mixture of acetonitrile and isopropanol is treated at 0°-5° with 0.7 g of 3-chloroperbenzoic acid and stirred for 2 hours. The reaction product is worked up as usual (see Example 71) and the crude product is purified by column chromatography (silica gel; elution with a 4:1-mixture of methylene chloride and methyl acetate), to yield the colourless, foamy 3-(5-diphenylmethoxycarbonyl-furfuryl)-7β-phenylacetylamino-ceph-3-em-4-carboxylic acid diphenylmethyl ester 1-oxide; thin-layer chromatogram (silica gel); Rf = 0.43 (system: toluene/acetone 4:1) and Rf = 0.53 (system: toluene/ethyl acetate 4:1); ultraviolet absorption spectrum (in 95% aqueous ethanol): λmax = 269-273 mμ (ε = 21000).

Workup

  1. customthe crude product is purified by column chromatography (silica gel
  2. washelution with a 4

Sources & evidence

ORD record
ord-7432a76266634ea78b3428acfaacaade
Source dataset
uspto-grants-1976_01
Patent number
US03932465

Reaction notes

Loading…