Hydrochloric Acid → HCID 88601110, compound

HRID 2413816Notes

Reaction equation

HRID 2413816 reaction equation
[CH:1]([NH:3][CH:4]1[C:32](=[O:33])[N:6]2[C:7]([C:16]([O:18][CH:19]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:17])=[C:8]([CH:12]=[C:13](Br)Br)[CH2:9][S:10](=[O:11])[C@H:5]12)=[O:2].C([Li])CCC.Cl>C(OCC)(=O)C>[CH:1]([NH:3][CH:4]1[C:32](=[O:33])[N:6]2[C:7]([C:16]([O:18][CH:19]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[O:17])=[C:8]([C:12]#[CH:13])[CH2:9][S:10](=[O:11])[C@H:5]12)=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 88600876HCID 88600876, compoundHCID 178418339Butyllithium

Product 1

HCID 88601110HCID 88601110, compoundYield 98.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution of benzhydryl 7-formamido-3-(2,2-dibromovinyl)-3-cephem-4-carboxylate-1-oxide (1.8 g) was added n-butyl lithium (7.27 ml of 1.65M solution in hexane) at -65° to -60° C. under a nitrogen atmosphere. After the resultant mixture was stirred at the same temperature for 30 minutes, ethyl acetate (50 ml) was added to the reaction mixture. The reaction mixture was warmed to -20° C., and hydrolysed with 10% hydrochloric acid. The organic layer was separated and washed with water and brine, dried over magnesium sulfate. The solution was evaporated in vacuo to give benzhydryl 7-formamido-3-ethynyl-3-cephem-4-carboxylate-1-oxide (1.30 g).

Workup

  1. customThe organic layer was separated
  2. washwashed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solution was evaporated in vacuo

Sources & evidence

ORD record
ord-169a1f6d81924586a4ae58bb45c5ec6b
Source dataset
uspto-grants-1988_01
Patent number
US04719206

Reaction notes

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