Acetic Acid → HCID 70524691, compound

HRID 1902509Notes

Reaction equation

HRID 1902509 reaction equation
[C:1]1([C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N+]=[N-])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:16]1([CH2:22][C:23]([NH:25][CH:26]2[C:38](=[O:39])[N:28]3[CH:29]([C:35]([OH:37])=[O:36])[CH:30]([CH2:33][OH:34])[CH2:31][S:32][C@H:27]23)=[O:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(O)(=O)C>C(OCC)(=O)C.O1CCCC1>[C:16]1([CH2:22][C:23]([NH:25][CH:26]2[C:38](=[O:39])[N:28]3[CH:29]([C:35]([O:37][CH:7]([C:10]4[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=4)[C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)=[O:36])[CH:30]([CH2:33][OH:34])[CH2:31][S:32][C@H:27]23)=[O:24])[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 612301,1'-(Diazomethylene)bis(benzene)HCID 70523673HCID 70523673, compound

Product 1

HCID 70524691HCID 70524691, compoundYield 24.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of diphenyldiazomethane (4 g.) in ethyl acetate was added to a stirred solution of 7-(2-phenylacetamido)-3-hydroxymethylcepham-4-carboxylic acid (7.0 g.) in ethyl acetate (100 ml.) and tetrahydrofuran (20 ml.), and stirred at room temperature for an hour. After adding acetic acid to the resultant solution, the solution was concentrated in vacuo. The residue was subjected to column chromatography on silica gel, and then eluted with a mixed solvent of ethyl acetate and diisopropyl ether. The eluate was evaporated in vacuo to give diphenylmethyl 7-(2-phenylacetamido)-3-hydroxymethylcepham-4-carboxylate (2.5 g.).

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. washeluted with a mixed solvent of ethyl acetate and diisopropyl ether
  3. customThe eluate was evaporated in vacuo

Sources & evidence

ORD record
ord-c1575cbe10b24f349e9a566c7b5ffe91
Source dataset
uspto-grants-1982_12
Patent number
US04363807

Reaction notes

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