Pyridine → HCID 13785486, compound

HRID 1905800Notes

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][CH2:19][CH:18]2[OH:36])=[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.N1C=CC=C[CH:38]=1.[C:43]1(C)[C:44]([S:49](Cl)(=[O:51])=[O:50])=[CH:45][CH:46]=[CH:47][CH:48]=1>ClCCl>[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][CH2:19][CH:18]2[O:36][S:49]([C:44]2[CH:43]=[CH:48][C:47]([CH3:38])=[CH:46][CH:45]=2)(=[O:50])=[O:51])=[O:16])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of 3-hydroxy-7beta-phenylacetylaminocepham-4-carboxylic acid diphenylmethyl ester (2) in dichloromethane (9 parts) cooling at 0° C. are added pyridine (6 equivalents) and toluenesulfonyl chloride (6 equivalents). The mixture is let stand at 0° to 5° C. for 105 hours. The reaction mixture is diluted with ice-water, the organic layer is taken, washed with hydrochloric acid and water, dried, and concentrated. The residue is crystallized from a mixture of ethyl acetate and hexane to give 3-p-toluenesulfonyloxy-7beta-phenylacetylaminocepham-4-carboxylic acid diphenylmethyl ester (3d). Yield: 84.7%. mp. 133°-136° C. (decomposition).

Workup

washwashed with hydrochloric acid and water
customdried
concentrationconcentrated
customThe residue is crystallized from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record: ord-1d0ce8eadadb4539acbb4ccdb8efda50
Source dataset: uspto-grants-1987_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04647658

Reaction notes

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