Ethanol → Ethyl 2-{[(benzyloxy)carbonyl]amino}-2-methylpropanoate

HRID 626910Notes

Reaction equation

HRID 626910 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]([CH3:17])([CH3:16])[C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:18](O)[CH3:19].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]([NH:11][C:12]([CH3:17])([CH3:16])[C:13]([O:15][CH2:18][CH3:19])=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 6101p-Toluenesulfonic acidHCID 294936N-((Benzyloxy)carbonyl)-2-methylalanine

Product 1

HCID 89649322Ethyl 2-{[(benzyloxy)carbonyl]amino}-2-methylpropanoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-(benzyloxycarbonylamino)-2-methyl-propanoic acid (which may be prepared as described in Description 32) (5000 mg, 21.08 mmol) in toluene (50 mL) was added ethanol (5 mL) and p-toluenesulfonic acid (400.89 mg, 2.11 mmol). The solution was stirred at 80° C. overnight. The reaction mixture was evaporated and the residues dissolved in EtOAc and washed with saturated aqueous sodium bicarbonate. The aqueous phase was back extracted into EtOAc. The combined organics were dried over magnesium sulphate, filtered and evaporated to yield the title compound (D33) as a light yellow oil (4.667 g);

Workup

  1. customThe reaction mixture was evaporated
  2. dissolutionthe residues dissolved in EtOAc
  3. washwashed with saturated aqueous sodium bicarbonate
  4. extractionThe aqueous phase was back extracted into EtOAc
  5. dry with materialThe combined organics were dried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-38ecc2c76ad4451e9e7eee9c30d8b720
Source dataset
uspto-grants-2016_04
Patent number
US09309254B2

Reaction notes

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