Benzyl chloroformate → Ethyl 2-(((benzyloxy)carbonyl)amino)-2-cyanoacetate

HRID 1661867Notes

Reaction equation

HRID 1661867 reaction equation
[C:1]([C:3](=[N:9]O)[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].C(=O)(O)[O-].[Na+].S(S([O-])=O)([O-])=O.[Na+].[Na+].[CH2:24]([O:31][C:32](Cl)=[O:33])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O>[CH2:24]([O:31][C:32]([NH:9][CH:3]([C:1]#[N:2])[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[O:33])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 10387Benzyl chloroformateHCID 24489Sodium DithioniteHCID 516892Sodium BicarbonateHCID 6399078Ethyl 2-cyano-2-(hydroxyimino)acetate

Product 1

HCID 9943163Ethyl 2-(((benzyloxy)carbonyl)amino)-2-cyanoacetateYield 64.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

To a mixture of ethyl 2-cyano-2-hydroxyiminoacetate (100 g, 0.704 mol) and water (600 ml), were added a saturated aqueous solution of sodium bicarbonate (200 ml) and sodium hydrosulfite (340 g, 1.96 mol) under ice-cooling, and then benzyloxycarbonyl chloride (144 g, 0.848 mol) was added dropwise under ice-cooling. After the addition was completed, the reaction solution was stirred at 20-30° C. for about 4 hours. Completion of the reaction was confirmed using TLC shown below, precipitated crystals were collected by filtration and washed with sprayed water (50 ml×3). The obtained crystals were recrystallized from ethanol (600 ml), filtered and washed with sprayed ethanol (50 ml×3), dried in airflow at 40° C. to give ethyl 2-benzyloxycarbonylamino-2-cyanoacetate (118.7 g, yield 64.2%).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. additionAfter the addition
  4. customprecipitated crystals
  5. filtrationwere collected by filtration
  6. washwashed with sprayed water (50 ml×3)
  7. customThe obtained crystals were recrystallized from ethanol (600 ml)
  8. filtrationfiltered
  9. washwashed with sprayed ethanol (50 ml×3)
  10. customdried in airflow at 40° C.

Sources & evidence

ORD record
ord-83269a8392d74a1d84eea365140d2ce4
Source dataset
uspto-grants-2011_10
Patent number
US08030486B2

Reaction notes

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