Acetic Acid → HCID 70503795, compound

HRID 1903572Notes

Reaction equation

HRID 1903572 reaction equation
[BH4-].[Na+].[N+:3]([C:6]1[CH:39]=[CH:38][C:9]([CH2:10][O:11][C:12]([C:14]2[N:19]3[C:20](=[O:31])[C@@H:21]([NH:22][C:23](=[O:30])[CH2:24][C:25]4[S:26][CH:27]=[CH:28][CH:29]=4)[C@H:18]3[S:17](=O)[CH2:16][C:15]=2N2CCCC2)=[O:13])=[CH:8][CH:7]=1)([O-:5])=[O:4].C(O)(=O)C>C(COC)OC.[Ti](Cl)(Cl)(Cl)Cl>[N+:3]([C:6]1[CH:7]=[CH:8][C:9]([CH2:10][O:11][C:12]([C:14]2[N:19]3[C:20](=[O:31])[C@@H:21]([NH:22][C:23](=[O:30])[CH2:24][C:25]4[S:26][CH:27]=[CH:28][CH:29]=4)[C@H:18]3[S:17][CH2:16][CH:15]=2)=[O:13])=[CH:38][CH:39]=1)([O-:5])=[O:4]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 70503948HCID 70503948, compound

Product 1

HCID 70503795HCID 70503795, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 80711,2-DimethoxyethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

To a mixture of 9.5 g (50 mmols) of titanium(IV) chloride and 5.67 g (150 mmols) of sodium borohydride in 150 ml of dimethoxy ethane is slowly added, at -20° C., a suspension of 10.86 g (20 mmols) of 7β-[2-(2-thienyl)-acetylamino]-3-pyrrolidino-3-cephem-4-carboxylic acid p-nitrobenzyl ester 1-oxide in 150 ml of ethylene glycol dimethyl ether, so that the temperature does not rise above -15° C. When the addition is complete, the reaction mixture is warmed to 0° C. and then a mixture of 50 ml of glacial acetic acid and 50 ml of ethylene glycol dimethyl ether is added dropwise. The reaction mixture is then stirred for 36 hours at room temperature. While cooling with ice, 200 ml of ice-water are cautiously added dropwise to the blue reaction solution. After extraction with three 150 ml portions of methylene chloride, the organic phase is dried over sodium sulfate and the solvent is removed by vacuum distillation, affording almost pure 7β-[2-(2-thienyl)-acetylamino]-3-cephem-4-carboxylic acid p-nitrobenzyl ester as a foam.

Workup

  1. additionis slowly added, at -20° C.
  2. customdoes not rise above -15° C
  3. additionWhen the addition
  4. additionis added dropwise
  5. additionare cautiously added dropwise to the blue reaction solution
  6. extractionAfter extraction with three 150 ml portions of methylene chloride
  7. dry with materialthe organic phase is dried over sodium sulfate
  8. customthe solvent is removed by vacuum distillation

Sources & evidence

ORD record
ord-2208a26fce174319bb654db8a6375a74
Source dataset
uspto-grants-1984_03
Patent number
US04436903

Reaction notes

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