Hydrochloric Acid → HCID 70635772, compound

HRID 596825Notes

Reaction equation

HRID 596825 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:37](=[O:38])[N:13]3[C:14]([C:21]([O:23][CH:24]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[O:22])=[C:15]([C:18](Cl)=[O:19])[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:39]([Li])[CH2:40][CH2:41][CH3:42].O1CCCC1.Cl>C(OCC)(=O)C>[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:37](=[O:38])[N:13]3[C:14]([C:21]([O:23][CH:24]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[O:22])=[C:15]([C:18](=[O:19])[CH2:39][CH2:40][CH2:41][CH3:42])[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 88819591HCID 88819591, compound2×HCID 178418339Butyllithium2×

Product 1

HCID 70635772HCID 70635772, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

The reaction of these carbanionic reagents with activated 3-carboxycephem intermediates (acid chlorides and mixed anhydrides) is carried out under the same conditions as discussed hereinabove for the process of this invention. A typical procedure is illustrated by reaction of benzhydryl 7-phenylacetamido-3-chlorocarbonyl-3-cephem-4-carboxylate with n-butyllithium. A ethereal solution of 3 equivalents of n-butyllithium is added to a solution of 1 mmole of benzhydryl 7-phenylacetamido-3-chlorocarbonyl-3-cephem-4-carboxylate in 30 ml. of tetrahydrofuran at -73° C. After approximately 5 minutes 10 ml. of 1N. hydrochloric acid is added, and the acidified mixture is then allowed to warm to about 0° C. Ethyl acetate is added, and the resulting mixture is washed with dilute hydrochloric acid and brine and dried over anhydrous sodium sulfate. Chromatographic purification provides benzhydryl 7-phenylacetamido-3-valeroyl-3-cephem-4-carboxylate.

Workup

  1. customat -73° C
  2. washthe resulting mixture is washed with dilute hydrochloric acid and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customChromatographic purification

Sources & evidence

ORD record
ord-03533bd3791248a2a61a73f429140b1f
Source dataset
uspto-grants-1977_03
Patent number
US04012380

Reaction notes

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