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

HRID 2420005Notes

Reaction equation

HRID 2420005 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>C(OCC)(=O)C>[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

4

Reactant 2

HCID 996PhenolHCID 20312395HCID 20312395, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Alternatively, N-t-Butoxycarbonyl-2-phenoxyglycine-n-butyl ester was prepared by heating a mixture of 1.5 g. (0.005 mol.) of N-t-butoxycarbonyl-2-acetoxyglycine n-butyl ester and 0.5 g. (0.005 mol.) of phenol at 150° for 1 hour. The residue was dissolved in ethyl acetate and the resulting solution was washed with cold 10% aqueous sodium hydroxide, dried (MgSO4) and concentrated to give the title compound.

Workup

  1. customAlternatively, N-t-Butoxycarbonyl-2-phenoxyglycine-n-butyl ester was prepared
  2. temperatureby heating
  3. additiona mixture of 1.5 g
  4. washthe resulting solution was washed with cold 10% aqueous sodium hydroxide
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-40e6dbc979da478fa8a5b1db4e73ba95
Source dataset
uspto-grants-1978_08
Patent number
US04108854

Reaction notes

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