Diethyl Ether → 3-(((Benzyloxy)carbonyl)amino)-3-methylbutanoic acid

HRID 1697059Notes

Reaction equation

HRID 1697059 reaction equation
[NH2:1][C:2]([CH3:8])([CH3:7])[CH2:3][C:4]([OH:6])=[O:5].Cl[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11].CCOCC>[OH-].[Na+]>[CH2:13]([O:12][C:10]([NH:1][C:2]([CH3:8])([CH3:7])[CH2:3][C:4]([OH:6])=[O:5])=[O:11])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 10387Benzyl chloroformateHCID 27609333-Amino-3-methylbutanoic acid

Product 1

HCID 145510073-(((Benzyloxy)carbonyl)amino)-3-methylbutanoic acidYield 46%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

3-Amino-3-methylbutyric acid (2.40 g, 20.49 mmol) was dissolved in NaOH (2 M aq, 35 mL), the resulting mixture cooled to 0° C., and benzyl chloroformate (5.77 mL, 40.97 mmol) added. The reaction mixture was stirred vigorously at 0° C. for 1 h and at RT for 3 h. Et2O (50 mL) was then added, and the layers separated. The organic layer was discarded. The aqueous layer was acidified to pH 2, brine added, and the resulting mixture extracted with EtOAc. The combined organic extracts were dried over anhydrous Na2SO4, filtered and evaporated under reduced pressure to give 3-benzyloxycarbonylamino-3-methyl-butyric acid (2.33 g, 46% yield) without further purification.

Workup

  1. customthe layers separated
  2. additionadded
  3. extractionthe resulting mixture extracted with EtOAc
  4. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-4d2a83d5127f4cdfa4a1d0eefeb89645
Source dataset
uspto-grants-2012_04
Patent number
US08163906B2

Reaction notes

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