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Methanol → Benzhydryl 7-Amino-3-chloromethyl-3-cephem-4-carboxylate

HRID 1681450
Notes
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Reaction equation

HRID 1681450 reaction equation
N1C=CC=CC=1.C1(CC([NH:16][CH:17]2[C:42](=[O:43])[N:19]3[C:20]([C:26]([O:28][CH:29]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[O:27])=[C:21]([CH2:24]O)[CH2:22][S:23][C@H:18]23)=O)C=CC=CC=1.P(Cl)(Cl)(Cl)(Cl)[Cl:45].CO>C(Cl)Cl>[NH2:16][CH:17]1[C:42](=[O:43])[N:19]2[C:20]([C:26]([O:28][CH:29]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:27])=[C:21]([CH2:24][Cl:45])[CH2:22][S:23][C@H:18]12
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 24819Phosphorus pentachlorideHCID 13339796Benzhydryl 3-hydroxymethyl-7-phenylacetamido-3-cephem-4-carboxylate

Product 1

HCID 13239626Benzhydryl 7-Amino-3-chloromethyl-3-cephem-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Conditions

Temperature
-20 °C

Procedure

19.64 ml (0.242 mol) of pyridine are added to a suspension of 50 g (0.0972 mol) of benzhydryl 7-phenylacetamido-3-hydroxymethyl-3-cephem-4-carboxylate in 500 ml of methylene chloride at room temperature. After cooling to -20° C., 40.48 g (0.0972 mol) of phosphorus pentachloride are added and the mixture is stirred at -20° C. for 5 minutes. The mixture is warmed to 0° C. with an icebath and stirred for 10 minutes, and is then warmed to 15° C. with a waterbath and stirred for 1 hour. Thereafter, the mixture is cooled to -70° C. and 720 ml of cold methanol are quickly added The mixture is then stirred at -70° C. for 5 minutes, at 0° C. for 10 minutes and at +15° C. for 25 minutes. The solution is subsequently concentrated to a high degree in vacuo and 1,400 ml of saturated sodium bicarbonate solution are added. The solution is extracted three times with methylene chloride and the organic phase is dried with sodium sulphate and concentrated in vacuo. The crude product is chromatographed on 500 g of silica gel 60 (0.04-0.063 mm) with methylene chloride.

Workup

  1. temperatureThe mixture is warmed to 0° C. with an icebath
  2. stirringstirred for 10 minutes
  3. temperatureis then warmed to 15° C. with a waterbath
  4. stirringstirred for 1 hour
  5. temperatureThereafter, the mixture is cooled to -70° C.
  6. stirringis then stirred at -70° C. for 5 minutes, at 0° C. for 10 minutes and at +15° C. for 25 minutes
  7. concentrationThe solution is subsequently concentrated to a high degree in vacuo and 1,400 ml of saturated sodium bicarbonate solution
  8. additionare added
  9. extractionThe solution is extracted three times with methylene chloride
  10. dry with materialthe organic phase is dried with sodium sulphate
  11. concentrationconcentrated in vacuo
  12. customThe crude product is chromatographed on 500 g of silica gel 60 (0.04-0.063 mm) with methylene chloride

Sources & evidence

ORD record
ord-f7fa88ce9c704db4b8df998686534428
Source dataset
uspto-grants-1992_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05171854

Reaction notes

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