Benzyl chloroformate → Tert-butyl 2-{[(benzyloxy)carbonyl](2-hydroxyethyl)amino}acetate

HRID 54616Notes

Reaction equation

HRID 54616 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]([O:11][C:12](=[O:18])[CH2:13][NH:14][CH2:15][CH2:16][OH:17])([CH3:10])([CH3:9])[CH3:8].Cl[C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21]>O1CCOCC1.O>[C:7]([O:11][C:12](=[O:18])[CH2:13][N:14]([C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21])[CH2:15][CH2:16][OH:17])([CH3:10])([CH3:8])[CH3:9]

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 11062917Tert-butyl 2-[(2-hydroxyethyl)amino]acetate

Product 1

HCID 19959626Tert-butyl 2-{[(benzyloxy)carbonyl](2-hydroxyethyl)amino}acetate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

Potassium carbonate (33.0 g; 0.19 mol) is added to a solution of the product from Example 4 (32.15 g; 0.18 mol) in dioxane (1.0 l) and water (0.5 l). A solution of benzyl chloroformate (27.3 ml; 0.19 mol) in dioxane (0.2 l) is slowly added dropwise at room temperature. The solution is stirred at room temperature for 3.5 h and subsequently concentrated. The residue is taken up in dichloromethane (3.0 l) and extracted by shaking with water (1.0 l). The aqueous phase is re-extracted five times with dichloromethane. The organic phases are combined, dried (magnesium sulphate) and concentrated. Yield: 24.47 g (43%), pale yellow oil.

Workup

  1. concentrationsubsequently concentrated
  2. extractionextracted
  3. stirringby shaking with water (1.0 l)
  4. extractionThe aqueous phase is re-extracted five times with dichloromethane
  5. dry with materialdried (magnesium sulphate)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f31902eeb5054acdbce1082f9b8c1bae
Source dataset
uspto-grants-1997_04
Patent number
US05623049

Reaction notes

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