Hydrochloric Acid → HCID 70636145, compound

HRID 596843Notes

Reaction equation

HRID 596843 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:35](=[O:36])[N:12]2[CH:13]([C:19]([O:21][CH:22]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:20])[C:14]([CH:17]=[O:18])=[CH:15][S:16][C@H:11]12)=[O:8].O1CC[CH2:39][CH2:38]1.C([Mg]Br)C.Cl>C(OCC)(=O)C>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:35](=[O:36])[N:12]2[CH:13]([C:19]([O:21][CH:22]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:20])[C:14]([CH:17]([OH:18])[CH2:38][CH3:39])=[CH:15][S:16][C@H:11]12)=[O:8]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 8028TetrahydrofuranHCID 88777142HCID 88777142, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 70636145HCID 70636145, compoundYield 30.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-73 °C

Procedure

To a cooled (-73° C.), stirred solution of 1.559 g. of benzhydryl 7-(2-thienylacetamido)-3-formyl-2-cephem-4-carboxylate and 20 ml. of dry tetrahydrofuran was added 3.13 ml. of 2.88 M. ethyl magnesium bromide. After the reaction mixture was allowed to stir for four minutes at -73° C., 10 ml. of 1N.HCl was added and the solution allowed to warm to 0° C. The reaction mixture was transferred to a separatory funnel with the aid of cold ethyl acetate and cold 1N.HCl. The organic layer was separated and washed twice with cold 1N.HCl and twice with brine and then dried over anhydrous sodium sulfate. Evaporation in vacuo to dryness provided a product residue which was chromatographed on silica gel using a toluene-ethyl acetate gradient to give 0.140 g. of the starting 3-formyl-2-cephem ester and 0.507 g. (30.6 percent) of the title product as a mixture of diasteromers:

Workup

  1. stirringto stir for four minutes at -73° C.
  2. temperatureto warm to 0° C
  3. customThe organic layer was separated
  4. washwashed twice with cold 1N
  5. dry with materialHCl and twice with brine and then dried over anhydrous sodium sulfate
  6. customEvaporation in vacuo to dryness
  7. customprovided a product residue which
  8. customwas chromatographed on silica gel using a toluene-ethyl acetate gradient
  9. customto give 0.140 g

Sources & evidence

ORD record
ord-e4f5ddd6e0e34fef81046c8671477ac0
Source dataset
uspto-grants-1977_03
Patent number
US04012380

Reaction notes

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