Benzyl chloroformate → HCID 57678048, compound

HRID 491821Notes

Reaction equation

HRID 491821 reaction equation
[C:1]([O:5][C:6](=[O:18])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][C:10]=1[C:16]#[N:17])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])O.[Na+].Cl[C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26]>O1CCCC1>[C:1]([O:5][C:6](=[O:18])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:25]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:26])=[CH:11][C:10]=1[C:16]#[N:17])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 57678171HCID 57678171, compound

Product 1

HCID 57678048HCID 57678048, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

t-Butyl(4-amino-2-cyanophenoxy)acetate (430 mg) obtained in Reference Example 50(1) is dissolved in tetrahydrofuran (10 ml), is added saturated sodium hydrogen carbonate solution (10 ml), and then is added benzyl chloroformate (355 mg) under ice-cooling. Under ice-cooling, the reaction solution is stirred for 1 hour and extracted with ethyl acetate. The organic layer is washed with saturated brine, dried over sodium sulfate, evaporated to remove the solvent under reduced pressure. The resulting residue is purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=9/1 followed by 3/1) to give t-butyl(4-benzyloxycarbonylamino-2-cyanophenoxy)acetate (540 mg).

Workup

  1. temperaturecooling
  2. temperatureUnder ice-cooling
  3. extractionextracted with ethyl acetate
  4. washThe organic layer is washed with saturated brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customto remove the solvent under reduced pressure
  8. customThe resulting residue is purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=9/1 followed by 3/1)

Sources & evidence

ORD record
ord-59576c8565eb4af4bbc2d39bd8866824
Source dataset
uspto-grants-2009_05
Patent number
US07531537B2

Reaction notes

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