Potassium Carbonate → methyl N-{3-[(tert-butoxycarbonyl)amino]-2-methylpropyl}-D-alaninate

HRID 854278Notes

Reaction equation

HRID 854278 reaction equation
[CH3:1][CH:2]([CH:12]=O)[CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].Cl.[CH3:15][O:16][C:17](=[O:21])[C@@H:18]([CH3:20])[NH2:19].C(=O)([O-])[O-].[K+].[K+].C([BH3-])#N.[Na+]>C(O)C>[C:7]([O:6][C:5]([NH:4][CH2:3][CH:2]([CH3:1])[CH2:12][NH:19][C@@H:18]([C:17]([O:16][CH3:15])=[O:21])[CH3:20])=[O:11])([CH3:8])([CH3:9])[CH3:10]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 5003444Sodium cyanoborohydrideHCID 11182647Methyl D-alaninate hydrochlorideHCID 19791000tert-butyl N-(2-methyl-3-oxopropyl)carbamate

Product 1

HCID 86607768methyl N-{3-[(tert-butoxycarbonyl)amino]-2-methylpropyl}-D-alaninate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of tert-butyl (2-methyl-3-oxopropyl)carbamate (2.0 g, 8.9 mmol) in ethanol was added D-Alanine methyl ester hydrochloride (1.25 g, 8.9 mmol), followed by potassium carbonate (0.62 g, 4.5 mmol). The resulting mixture was stirred at room temperature for 3 hr. Sodium cyanoborohydride (0.63 g, 10 mmol) was added in one portion. The reaction mixture was stirred at room temperature overnight. The solvent was removed on a rotavap, and the residue was taken up into water and extracted with ethyl acetate (3×). The combined organic extract was washed with brine, dried over sodium sulfate and evaporated to yield methyl N-{3-[(tert-butoxycarbonyl)amino]-2-methylpropyl}-D-alaninate as colorless viscous oil, which was used without further purification. MS (M+1−Boc): 175.3

Workup

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. customThe solvent was removed on a rotavap
  3. extractionextracted with ethyl acetate (3×)
  4. extractionThe combined organic extract
  5. washwas washed with brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-d3e98c2a8d6f4a09b5bb1af9cc59536b
Source dataset
uspto-grants-2007_08
Patent number
US07259160B2

Reaction notes

Loading…