Sodium Carbonate → (S)-Methyl 2-(((benzyloxy)carbonyl)amino)-4-methylpentanoate

HRID 1977465Notes

Reaction equation

HRID 1977465 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:11])[C@H:5]([CH2:7][CH:8]([CH3:10])[CH3:9])[NH2:6].C([O-])([O-])=O.[Na+].[Na+].[CH2:18]([O:25][C:26](Cl)=[O:27])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O1CCOCC1>[CH3:2][O:3][C:4](=[O:11])[C@H:5]([CH2:7][CH:8]([CH3:10])[CH3:9])[NH:6][C:26]([O:25][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:27]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 2723695Leucine methyl ester hydrochloride

Product 1

HCID 2063832(S)-Methyl 2-(((benzyloxy)carbonyl)amino)-4-methylpentanoateYield 100.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirring solution of L-leucine methyl ester hydrochloride (2.0 g, 11.0 mmol), in 1,4-dioxane (20 mL) was added Na2CO3 (12.1 ml, 2M in water) followed by benzylchloroformate (1.96 g, 11.5 mmol). The mixture was stirred at room temperature for 4 h then partitioned between ethyl acetate and water. The organic layer was washed with brine, dried (MgSO4), filtered and concentrated to yield the title compound as a colorless oil (3.1 g, 100%). 1H NMR (400 MHz, CDCl3) δ 7.34 (m, 5H), 5.27 (d, 1H), 5.12 (s, 2H), 4.41 (s, 2H), 3.75 (s, 3H), 1.65 (m, 3H), 0.96 (m, 6H).

Workup

  1. customthen partitioned between ethyl acetate and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9d8809b46742488b97631fc993f32459
Source dataset
uspto-grants-2001_05
Patent number
US06232342B1

Reaction notes

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