L-Isoleucine → L-Isoleucine, N-(methoxycarbonyl)-

HRID 2364873Notes

Reaction equation

HRID 2364873 reaction equation
[NH2:1][C@@H:2]([C@@H:6]([CH3:9])[CH2:7][CH3:8])[C:3]([OH:5])=[O:4].[OH-].[Na+].Cl[C:13]([O:15][CH3:16])=[O:14]>O1CCOCC1.CCOC(C)=O>[CH3:16][O:15][C:13]([NH:1][C@@H:2]([C@@H:6]([CH3:9])[CH2:7][CH3:8])[C:3]([OH:5])=[O:4])=[O:14]

Participants

6

Reactant 3

HCID 6306L-IsoleucineHCID 6586Methyl chloroformateHCID 14798Sodium Hydroxide

Product 1

HCID 28378062L-Isoleucine, N-(methoxycarbonyl)-Yield 97.1%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of (2S,3S)-2-amino-3-methylpentanoic acid (1.0 g, 7.62 mmol) in dioxane (10 mL) at 0° C. was added NaOH (12.58 g, 25.2 mmol) followed by dropwise addition of methyl chloroformate (1.18 mL, 15.25 mmol). The solution was warmed to room temperature with stirring over 2 h, diluted with EtOAc, washed with 1 N HCl, brine, dried (Na2SO4), filtered and solvent removed in vacuo to give the title compound (1.4 g, 7.4 mmol, 97%). 1H NMR (400 MHz, CDCl3) δ ppm 1.27-1.39 (m, 1H) 1.38-1.53 (m, 2 H) 1.58-1.72 (m, 3H) 1.82-1.94 (m, 2H) 2.04 (d, J=3.8 Hz, 2H) 3.70 (s, 3H) 4.94 (br s, 1H).

Workup

  1. washwashed with 1 N HCl, brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customsolvent removed in vacuo

Sources & evidence

ORD record
ord-119f0244cb6b431b962790889eaeb09f
Source dataset
uspto-grants-2014_04
Patent number
US08691938B2

Reaction notes

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