Pyridine → Ethyl 2-(((benzyloxy)carbonyl)amino)-2-cyanoacetate

HRID 256598

Reaction equation

HRID 256598 reaction equation
[CH2:1]([O:3][C:4](=[O:9])[CH:5]([NH2:8])[C:6]#[N:7])[CH3:2].N1C=CC=CC=1.[CH2:16]([O:23][C:24](Cl)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>O>[CH2:1]([O:3][C:4](=[O:9])[CH:5]([NH:8][C:24]([O:23][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:25])[C:6]#[N:7])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 10387Benzyl chloroformateHCID 288716Ethyl 2-amino-2-cyanoacetate

Product 1

HCID 9943163Ethyl 2-(((benzyloxy)carbonyl)amino)-2-cyanoacetateYield 60.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred mixture of 2-amino-2-cyanoacetic acid ethyl ester (19.7 g) and pyridine (12.2 g) in water (123 ml) was added portionwise benzyloxycarbonyl chloride (27.9 g) under ice cooling. The resulting mixture was stirred under ice cooling for 1 hour. Precipitated crystals were collected, washed thoroughly with water, and recrystallized from ethanol to give the title compound (24.2 g, 60.2%) as colorless crystals, mp 111°-112° C.

Workup

  1. customPrecipitated crystals
  2. customwere collected
  3. washwashed thoroughly with water
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-4ea026a1293a48e196c3c781eb05705b
Source dataset
uspto-grants-1993_11
Patent number
US05258382

Linked notes

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