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

HRID 2270486Notes

Reaction equation

HRID 2270486 reaction equation
[CH3:1][O:2][C:3](=[O:10])[C@H:4]([CH2:6][CH:7]([CH3:9])[CH3:8])[NH2:5].C([O-])([O-])=O.[Na+].[Na+].[CH2:17]([O:24][C:25](Cl)=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O1CCOCC1>[CH3:1][O:2][C:3](=[O:10])[C@H:4]([CH2:6][CH:7]([CH3:9])[CH3:8])[NH:5][C:25]([O:24][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:26]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 65105(+)-L-Leucine methyl ester

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 (2.0 g, 11.0 mmol) in 1,4 dioxane (20 mL) was added aqueous Na2CO3 solution (12.1 mL, 2M in H2O) followed by benzylchloroformate (1.96 g, 11.5 mmol). The mixture stirred at room temperature for 4 h then partitioned between ethyl acetate and water. The organic layer was washed with saturated brine, dried (MgSO4), filtered and concentrated to yield the title compound as a colorless oil (3.1 g, 100%). 1HNMR (400 MHz, CDCl3) δ7.34 (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 saturated brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-15ccdb1341d54a30b9c8bc49e342f2a2
Source dataset
uspto-grants-2001_12
Patent number
US06331542B1

Reaction notes

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