Methanol → HCID 67899089, compound

HRID 1681454Notes

Reaction equation

HRID 1681454 reaction equation
C1(CC([NH:10][CH:11]2[C:33](=[O:34])[N:13]3[C:14]([C:21]([O:23][CH2:24][C:25]4[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=4)=[O:22])=[C:15](/[CH:18]=[CH:19]\[CH3:20])[CH2:16][S:17][C@H:12]23)=O)C=CC=CC=1.N1C=CC=CC=1.P(Cl)(Cl)(Cl)(Cl)Cl.CO>C(Cl)Cl>[NH2:10][CH:11]1[C:33](=[O:34])[N:13]2[C:14]([C:21]([O:23][CH2:24][C:25]3[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=3)=[O:22])=[C:15](/[CH:18]=[CH:19]\[CH3:20])[CH2:16][S:17][C@H:12]12

Participants

6

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 24819Phosphorus pentachlorideHCID 68863050HCID 68863050, compound

Product 1

HCID 67899089HCID 67899089, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-50 °C

Procedure

12.1 g (25.28 mmol) of p-methoxybenzyl 7-phenylacetamido-3-[(Z)-propen-1-yl]-3-cephem-4-carboxylate (Example 15) are dissolved in 133 ml of methylene chloride, the solution is cooled to -50° C. and 5.11 ml (63.2 mmol) of pyridine and 5.26 g (25.28 mmol) of phosphorus pentachloride are added in succession. The temperature is then allowed to rise to -10° C. in the course of 25 minutes. After a further 20 minutes, the temperature of the solution is 0° C.; thereafter, the solution is stirred to +15° C. for a further 45 minutes. The mixture is now cooled to -50° C., 200 ml of methanol (about -30° C.) are added all at once and the mixture is stirred for 30 minutes, without cooling. The reaction solution is concentrated, the oily residue is dissolved in methylene chloride and the solution is introduced onto a column packed with 400 ml of silica gel (0.04-0.063 mm). The column is eluted first with methylene chloride and then with the solvent mixtures methylene chloride--5% methanol and methylene chloride--10% methanol in succession. The fractions which are eluted with the methylene chloride--10% methanol mixture are concentrated to dryness.

Workup

  1. customto rise to -10° C. in the course of 25 minutes
  2. customis 0° C.
  3. temperatureThe mixture is now cooled to -50° C.
  4. stirringis stirred for 30 minutes
  5. temperaturewithout cooling
  6. concentrationThe reaction solution is concentrated
  7. dissolutionthe oily residue is dissolved in methylene chloride
  8. additionthe solution is introduced onto a column
  9. washThe column is eluted first with methylene chloride
  10. washThe fractions which are eluted with the methylene chloride--10% methanol mixture
  11. concentrationare concentrated to dryness

Sources & evidence

ORD record
ord-eee1a4bb651949ee835dd091f13b9361
Source dataset
uspto-grants-1992_12
Patent number
US05171854

Reaction notes

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