Diisopropyl Ether → HCID 88601107, compound

HRID 1380979Notes

Reaction equation

HRID 1380979 reaction equation
C([NH:3][CH:4]1[C:29](=[O:30])[N:6]2[C:7]([C:13]([O:15][CH:16]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:14])=[C:8]([C:11]#[CH:12])[CH2:9][S:10][C@H:5]12)=O.P(Cl)(Cl)(Cl)=O.C(OC(C)C)(C)C>CO.O1CCCC1>[NH2:3][CH:4]1[C:29](=[O:30])[N:6]2[C:7]([C:13]([O:15][CH:16]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:14])=[C:8]([C:11]#[CH:12])[CH2:9][S:10][C@H:5]12

Participants

6

Reactant 3

HCID 7914Diisopropyl EtherHCID 24813Phosphorus oxychlorideHCID 88600753HCID 88600753, compound

Product 1

HCID 88601107HCID 88601107, compoundYield 72.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzhydryl 7-formamido-3-ethynyl-3-cephem-4-carboxylate (3 g) in a mixture of methanol (30 ml) and tetrahydrofuran (15 ml) was added phosphorus oxychloride (2.75 g) under ice-cooling. After the resultant mixture was stirred at room temperature for 30 minutes, the reaction mixture was added to diisopropyl ether (300 ml), and the precipitates were collected by filtration. The precipitates were added to a mixture of water (50 ml) and ethyl acetate (50 ml) under stirring, and the mixture was adjusted to pH 7.0 with saturated aqueous sodium bicarbonate. To the separated aqueous layer was added ethyl acetate (50 ml), and the mixture was acidified to pH 3.0 with 10% hydrochloric acid and the resultant precipitates were collected by filtration to give benzhydryl 7-amino-3-ethynyl-3-cephem-4-carboxylate (2.03 g).

Workup

  1. temperaturecooling
  2. filtrationthe precipitates were collected by filtration
  3. additionThe precipitates were added to a mixture of water (50 ml) and ethyl acetate (50 ml)
  4. additionTo the separated aqueous layer was added ethyl acetate (50 ml)
  5. customthe resultant precipitates
  6. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-8e9058d666c8446ba0a21e11798f839b
Source dataset
uspto-grants-1986_04
Patent number
US04584290

Reaction notes

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