Chloroacetonitrile → Cyanomethyl 3-(t-butyloxycarbonylamino)benzoate

HRID 248687Notes

Reaction equation

HRID 248687 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([OH:14])=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:18]([N:20](CC)CC)[CH3:19].ClCC#N>CC(C)=O>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([O:14][CH2:19][C:18]#[N:20])=[O:13])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 8471TriethylamineHCID 8541623-(((Tert-butoxy)carbonyl)amino)benzoic acid

Product 1

HCID 8520682Cyanomethyl 3-(t-butyloxycarbonylamino)benzoateYield 99%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3-(t-butyloxycarbonylamino)benzoic acid (20 g), triethylamine (12.8 g), chloroacetonitrile (9.4 g) and acetone (150 ml) is refluxed for 4 hours. After acetone is distilled off under reduced pressure, the residue is dissolved in ethyl acetate (200 ml), and the solution is washed with water, and ethyl acetate is distilled off under reduced pressure. The residue is recrystallized from 80% aqueous acetonitrile solution to give the title compound (22 g, 99%) as white short needles.

Workup

  1. temperatureis refluxed for 4 hours
  2. distillationAfter acetone is distilled off under reduced pressure
  3. dissolutionthe residue is dissolved in ethyl acetate (200 ml)
  4. washthe solution is washed with water, and ethyl acetate
  5. distillationis distilled off under reduced pressure
  6. customThe residue is recrystallized from 80% aqueous acetonitrile solution

Sources & evidence

ORD record
ord-3e19f1e60acc46ec8b09a1422ac01bce
Source dataset
uspto-grants-1993_05
Patent number
US05210266

Reaction notes

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