Pyridine → HCID 11145881, compound

HRID 1788941Notes

Reaction equation

HRID 1788941 reaction equation
N1C=CC=CC=1.CN(C)C=O.S(Cl)([Cl:14])=O.O[CH2:17][C:18]1[CH2:19][S:20][C@@H:21]2[C@H:41]([NH:42][C:43](=[O:51])[CH2:44][C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[C:40](=[O:52])[N:22]2[C:23]=1[C:24]([O:26][CH:27]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25]>O1CCCC1>[Cl:14][CH2:17][C:18]1[CH2:19][S:20][C@@H:21]2[C@H:41]([NH:42][C:43](=[O:51])[CH2:44][C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[C:40](=[O:52])[N:22]2[C:23]=1[C:24]([O:26][CH:27]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 10864182HCID 10864182, compound

Product 1

HCID 11145881HCID 11145881, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

24 ml (0.3 mole) of pyridine, 400 μl of dimethylformamide and 21.6 ml (0.3 mole) of thionyl chloride are added to a solution of 103 g (0.2 mole) of benzhydryl 3-hydroxymethyl-7β-phenylacetamido-3-cephem-4-carboxylate (prepared, for example, in accordance with Helv. Chim. Acta 57, 2044 (1974)) in 3.5 l of absolute tetrahydrofuran, while cooling with ice. After 10 minutes, the mixture is concentrated on a rotary evaporator, the residue is taken up in 2 l of ethyl acetate and the mixture is extracted by shaking twice with sodium bicarbonate solution and once with water. The organic phase is extracted by stirring with 50 g each of kieselguhr and active charcoal and the extract is filtered with suction over a frit covered with silica gel. The filtrate is then dried over magnesium sulphate and concentrated, the residue is taken up in 200 ml of methylene chloride and the product is precipitated with petroleum ether.

Workup

  1. temperaturewhile cooling with ice
  2. concentrationthe mixture is concentrated on a rotary evaporator
  3. extractionthe mixture is extracted
  4. extractionThe organic phase is extracted
  5. stirringby stirring with 50 g each of kieselguhr and active charcoal
  6. filtrationthe extract is filtered with suction over a frit
  7. dry with materialThe filtrate is then dried over magnesium sulphate
  8. concentrationconcentrated
  9. customthe product is precipitated with petroleum ether

Sources & evidence

ORD record
ord-55a62297bd47465797a5e421f0df4cfa
Source dataset
uspto-grants-1987_08
Patent number
US04686216

Reaction notes

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