Toluene → HCID 13892058, compound

HRID 1903574Notes

Reaction equation

HRID 1903574 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[CH:14]([O:27][C:28]([C:30]1[N:35]2[C:36](=[O:49])[C@@H:37]([NH:38][C:39](=[O:48])[CH2:40][O:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[C@H:34]2[S:33][CH2:32][C:31]=1N1CCOCC1)=[O:29])([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C1(C)C=CC=CC=1>C(O)(=O)C>[CH:14]([O:27][C:28]([C:30]1[N:35]2[C:36](=[O:49])[C@@H:37]([NH:38][C:39](=[O:48])[CH2:40][O:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[C@H:34]2[S:33][CH2:32][CH:31]=1)=[O:29])([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 2724942TriacetoxyborohydrideHCID 44151031N-{2-[(Diphenylmethoxy)carbonyl]-3-(morpholin-4-yl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-7-yl}-2-phenoxyethanimidic acid

Product 1

HCID 13892058HCID 13892058, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
40 °C

Procedure

A suspension is prepared from 142 g (3.75 mmols) of sodium borohydride and 2.4 liters of abs. toluene and then 2.2 liters of glacial acetic acid are added over 4 hours at 20° C. The hydrogen formed during the exothermic reaction is drawn off. To the triacetoxy borohydride so formed are then added, at 20° C., 400 g (0.683 mmol) of 7β-phenoxyacetylamino-3-morpholino-3-cephem-4-carboxylic acid benzhydryl ester in 1.2 liters of glacial acetic acid and 600 ml of abs. toluene. The reaction mixture is warmed to 40° C. and then stirred for 24 hours at this temperature. The solvent is then removed completely by vacuum distillation and the oily residue is partitioned between 1.4 liters of water and 1.4 liters of toluene. The phases are separated and the aqueous phase is extracted with 600 ml of toluene. The combined organic phases are neutralised with saturated sodium bicarbonate solution and washed with two 50 ml portions of water. The organic phase is concentrated under reduced pressure and the oily residue is dissolved in 1.5 liters of ethanol at 55° C. Inoculation of the slowly cooling solution results in the crystallisation of 7β-phenoxyacetylamino-3-cephem-4-carboxylic acid benzhydryl ester.

Workup

  1. additionare then added, at 20° C.
  2. customThe solvent is then removed completely by vacuum distillation
  3. customthe oily residue is partitioned between 1.4 liters of water and 1.4 liters of toluene
  4. customThe phases are separated
  5. extractionthe aqueous phase is extracted with 600 ml of toluene
  6. washwashed with two 50 ml portions of water
  7. concentrationThe organic phase is concentrated under reduced pressure
  8. dissolutionthe oily residue is dissolved in 1.5 liters of ethanol at 55° C

Sources & evidence

ORD record
ord-bc1f7f8872a546869fa183c2476eb8c0
Source dataset
uspto-grants-1984_03
Patent number
US04436903

Reaction notes

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