L-Methionine → 16639-89-7

HRID 1471047Notes

Reaction equation

HRID 1471047 reaction equation
[NH2:1][C@@H:2]([CH2:6][CH2:7][S:8][CH3:9])[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]([CH2:6][CH2:7][S:8][CH3:9])[C:3]([OH:5])=[O:4])=[O:14]

Participants

6

Reactant 3

HCID 6137L-MethionineHCID 6586Methyl chloroformateHCID 14798Sodium Hydroxide

Product 1

HCID 994249816639-89-7Yield 94%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of (S)-2-amino-4-(methylthio)butanoic acid (1.0 g, 6.7 mmol) in dioxane at 0° C. was added NaOH (11.06 g, 22.12 mmol) followed by dropwise addition of methyl chloroformate (1.04 mL, 13.4 mmol) and the solution was warmed to room temperature with stirring over 2 h. The solution was diluted with EtOAc, washed with 1 N HCl, brine, dried (Na2SO4), filtered and solvent removed in vacuo to give the title compound (1.3 g, 6.27 mmol, 94%). 1H NMR (400 MHz, CDCl3) δ ppm 1.95-2.07 (m, 1H) 2.07-2.13 (m, 3H) 2.14-2.28 (m, 1H) 2.59 (t, J=7.4 Hz, 2H) 3.71 (s, 3H) 4.52 (br s, 1H) 5.33 (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-e894ed12c6164b45bf4623da5b121cc8
Source dataset
uspto-grants-2015_04
Patent number
US09006387B2

Reaction notes

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