Ethyl Acetate → HCID 14579395, compound

HRID 1607733Notes

Reaction equation

HRID 1607733 reaction equation
Br.[NH2:2][CH2:3][CH:4]([C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)[CH3:5].C(OCC)(=O)C.C(=O)([O-])[O-].[K+].[K+].[CH2:25]([O:32][C:33](Cl)=[O:34])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>O>[CH2:25]([O:32][C:33]([NH:2][CH2:3][CH:4]([C:6]1[CH:7]=[CH:8][C:9]([OH:12])=[CH:10][CH:11]=1)[CH3:5])=[O:34])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 14579478HCID 14579478, compound

Product 1

HCID 14579395HCID 14579395, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4.64 g of (±)-4-(2-amino-1-methylethyl)phenol hydrobromide, 100 ml of ethyl acetate, 6.92 g of potassium carbonate, 40 ml of water and 3.75 g of benzyloxycarbonyl chloride is stirred at room temperature overnight. After the reaction, the ethyl acetate layer is separated therefrom, washed, dried, and then evaporated under reduced pressure to remove the solvent. 4.82 g of (±)-4-(2-benzyloxycarbonylamino-1-methylethyl)phenol are obtained as pale yellow oil.

Workup

  1. customAfter the reaction
  2. customthe ethyl acetate layer is separated
  3. washwashed
  4. customdried
  5. customevaporated under reduced pressure
  6. customto remove the solvent

Sources & evidence

ORD record
ord-65d215a4ce064f279b0a1a1aa416cc97
Source dataset
uspto-grants-1989_09
Patent number
US04866196

Reaction notes

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