Acetic Acid → HCID 70502523, compound

HRID 1903571Notes

Reaction equation

HRID 1903571 reaction equation
[CH:1]([O:14][C:15]([C:17]1[N:22]2[C:23](=[O:36])[C@@H:24]([NH:25][C:26](=[O:35])[CH2:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C@H:21]2[S:20][CH2:19][C:18]=1N1CCOCC1)=[O:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)Cl.C(O)(=O)C.[BH4-].[Na+]>C(O)C>[CH:1]([O:14][C:15]([C:17]1[N:22]2[C:23](=[O:36])[C@@H:24]([NH:25][C:26](=[O:35])[CH2:27][CH2:28][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[C@H:21]2[S:20][CH2:19][CH:18]=1)=[O:16])([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 6344DichloromethaneHCID 4311764Sodium borohydrideHCID 70503657HCID 70503657, compound

Product 1

HCID 70502523HCID 70502523, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

11.4 g (20 mmols) of 7β-benzylacetylamino-3-morpholino-3-cephem-4-carboxylic acid benzhydryl ester are dissolved in 50 ml of ethanol, 50 ml of methylene chloride and 50 ml of glacial acetic acid. The solution is cooled to 0° C. and then, with stirring and under nitrogen, 4.08 g (120 mmols) of sodium borohydride are added in 200 mg portions over 1 hour, with vigorous evolution of gas after each addition. When the addition is complete, the reaction mixture is cooled to room temperature and, after addition of a further 50 ml of glacial acetic acid, stirred for 36 hours at room temperature. The clear, almost colourless solution is concentrated in a rotary evaporator and the residue is partitioned between water and methylene chloride. The organic phase is washed again with two 50 ml portions of water and then concentrated in vacuo, affording crude 7β-benzylacetylamino-3-cephem-4-carboxylic acid benzhydryl ester as a foam.

Workup

  1. additionafter each addition
  2. additionWhen the addition
  3. temperaturethe reaction mixture is cooled to room temperature
  4. stirringstirred for 36 hours at room temperature
  5. concentrationThe clear, almost colourless solution is concentrated in a rotary evaporator
  6. customthe residue is partitioned between water and methylene chloride
  7. washThe organic phase is washed again with two 50 ml portions of water
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-808bcb717e794483aa2f4dbd488491af
Source dataset
uspto-grants-1984_03
Patent number
US04436903

Reaction notes

Loading…