2,3-Dihydrofuran → HCID 131714475, compound

HRID 638339Notes

Reaction equation

HRID 638339 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].[O:35]1[CH:39]=[CH:38][CH2:37][CH2:36]1>>[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]=[C:36]3[CH2:37][CH2:38][CH2:39][O:35]3)[CH2:15][S:16][C@H:11]12)=[O:8]

Participants

3

Reactant 2

HCID 709342,3-DihydrofuranHCID 13564037HCID 13564037, compound

Product 1

HCID 131714475HCID 131714475, compound

Procedure

A mixture of 852 mg. of p-nitrobenzyl 7β-(2-thienylacetylamino)-3-azido-3-cephem-4-carboxylate and 20 ml. of 2,3-dihydrofuran was heated at the reflux temperature (54°-55° C.) for 15 minutes. The mixture was evaporated to dryness and the residue chromatographed over 8 g. of silica gel (toluene) using 400 ml. of 5% ethyl acetate in toluene vs. 400 ml. of ethyl acetate. Multiple fractions were collected and fractions containing the product were pooled and evaporated to dryness to give 559 mg. of the title compound.

Workup

  1. additionA mixture of 852 mg
  2. customThe mixture was evaporated to dryness
  3. customthe residue chromatographed over 8 g
  4. customwere collected
  5. additionfractions containing the product
  6. customevaporated to dryness
  7. customto give 559 mg

Sources & evidence

ORD record
ord-bd0fc691919740b4baabf66ec4f9adcf
Source dataset
uspto-grants-1985_12
Patent number
US04560749

Reaction notes

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