Acetone → HCID 13472291, compound

HRID 1248031Notes

Reaction equation

HRID 1248031 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][C@@H:10]1[C:33](=[O:34])[N:12]2[C:13]([C:20]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=3)=[O:21])=[C:14]([N:17]=[N+]=[N-])[CH2:15][S:16][C@H:11]12)=[O:8].[CH3:35][C:36](C)=[O:37]>C(O)C>[N+:30]([C:27]1[CH:28]=[CH:29][C:24]([CH2:23][O:22][C:20]([CH:13]2[N:17]=[C:14]([O:37][CH2:36][CH3:35])[CH2:15][S:16][CH:11]3[N:12]2[C:33](=[O:34])[CH:10]3[NH:9][C:7](=[O:8])[CH2:6][C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)=[O:21])=[CH:25][CH:26]=1)([O-:32])=[O:31]

Participants

4

Reactant 2

HCID 180AcetoneHCID 13564037HCID 13564037, compound

Product 1

HCID 13472291HCID 13472291, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2.53 g of p-nitrobenzyl 7β-[(2-thienylacetyl)amino]-3-azido-3-cephem-4-carboxylate in 50 ml. of acetone and 50 ml. of ethyl alcohol was heated at the reflux temperature for 1.25 hr. and thereafter the solution was evaporated to dryness. The crude product showed three spots on a thin layer chromatogram. The predominant 4-ethoxy-1,3-diaza isomer (title compound) was separated from the other isomer by chromatography over 15 g. of silica gel using 600 ml. of toluene vs 600 ml. of 75% ethyl acetate-toluene. The title compound was obtained crystalline as fine white needles (0.713 g.) melting at about 154° C. to about 155° C. after recrystallization from methylethyl ketone-hexane.

Workup

  1. customand thereafter the solution was evaporated to dryness
  2. customThe predominant 4-ethoxy-1,3-diaza isomer (title compound) was separated from the other isomer by chromatography over 15 g

Sources & evidence

ORD record
ord-9aa66f86a01b4824ba0eb90504e90294
Source dataset
uspto-grants-1985_06
Patent number
US04521598

Reaction notes

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