Phenol → Butyl [(tert-butoxycarbonyl)amino](phenoxy)acetate

HRID 2420004Notes

Reaction equation

HRID 2420004 reaction equation
[CH2:1]([O:5][C:6](=[O:20])[CH:7]([O:16][C:17](=O)[CH3:18])[NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:2][CH2:3][CH3:4].[C:21]1([O-])[CH:26]=CC=[CH:23][CH:22]=1.[Na+].C1(O)C=CC=CC=1.C[O-].[Na+]>O1CCOCC1>[CH2:1]([O:5][C:6](=[O:20])[CH:7]([O:16][C:17]1[CH:23]=[CH:22][CH:21]=[CH:26][CH:18]=1)[NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 996PhenolHCID 4445035Phenolate SodiumHCID 10942334Sodium MethoxideHCID 20312395HCID 20312395, compound

Product 1

HCID 20312412Butyl [(tert-butoxycarbonyl)amino](phenoxy)acetate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To 2.9 g (0.01 mol.) of N-t-butoxycarbonyl-2-acetoxyglycine n-butyl ester in 10 ml. of dioxane was added a solution of sodium phenolate prepared from 0.94 g. of phenol and 0.54 g. of sodium methoxide in 15 ml. of dioxane After refluxing for 2 hours, the solvent was evaporated in vacuo and the residue was dissolved in ethyl acetate. The ethyl acetate solution was washed with cold 10% aqueous sodium hydroxide, dried (MgSO4) and concentrated to yield the title compound as an oil.

Workup

  1. customprepared from 0.94 g
  2. customthe solvent was evaporated in vacuo
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe ethyl acetate solution was washed with cold 10% aqueous sodium hydroxide
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0e380813aa8d4acdb70274037c1b2f2d
Source dataset
uspto-grants-1978_08
Patent number
US04108854

Reaction notes

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