Pentane → (R)-Boc-N-Me-3-Amino-2-methylpropanoic acid

HRID 1588585Notes

Reaction equation

HRID 1588585 reaction equation
[C:1]([NH:8][CH2:9][CH:10]([CH3:14])[C:11]([OH:13])=[O:12])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:15]CCCC>C1COCC1>[CH3:15][N:8]([C:1]([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2])[CH2:9][C@@H:10]([CH3:14])[C:11]([OH:13])=[O:12]

Participants

4

Reactant 2

HCID 8003PentaneHCID 41926403-((tert-Butoxycarbonyl)amino)-2-methylpropanoic acid

Product 1

HCID 93898361(R)-Boc-N-Me-3-Amino-2-methylpropanoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-Boc-α-(R,S)-methyl-β-alanine (1.33 g, 6.5 mmol) in THF (80ml) was added pentane washed sodium hydride (1.2 g, 60% in oil dispersion) followed by methyl iodide (2 ml, exess). The reaction mixture was stirred overnight and then poured into an iced solution of citric acid (0.5N). The aqueous THF solution was extracted into ethyl acetate. Then the required acid was back extracted between ethyl acetate, sodium hydrogen carbonate and potassium hydrogen sulphate solutions. The organic extracts were dried (MgSO4) and evaporated to afford the title compound. (1.00 g, 71%), Anal: C10H19NO4.0.3H2O, Calc: C, 53.94; H, 8.87; N, 6.29. Found, C, 54.02; H, 8.56; N, 6.63.

Workup

  1. washwashed sodium hydride (1.2 g, 60% in oil dispersion)
  2. additionpoured into an iced solution of citric acid (0.5N)
  3. extractionThe aqueous THF solution was extracted into ethyl acetate
  4. extractionThen the required acid was back extracted between ethyl acetate, sodium hydrogen carbonate and potassium hydrogen sulphate solutions
  5. dry with materialThe organic extracts were dried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-84e528a9e3594c36be877fe80f3f4b7d
Source dataset
uspto-grants-1993_06
Patent number
US05223514

Reaction notes

Loading…