Water → (R)-2-Acetoxy-4-(methylthio)butyric Acid

HRID 2352050Notes

Reaction equation

HRID 2352050 reaction equation
N[C@@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH2:4][S:5][CH3:6].N([O-])=O.[Na+].O.[C:15]([O:18]CC)(=[O:17])[CH3:16]>C(O)(=O)C>[C:15]([O:18][C@H:2]([CH2:3][CH2:4][S:5][CH3:6])[C:7]([OH:9])=[O:8])(=[O:17])[CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 84815D-MethionineHCID 23668193Sodium Nitrite

Product 1

HCID 10954386(R)-2-Acetoxy-4-(methylthio)butyric Acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

D-Methionine (14.9 g, 0.10 mol) was stirred in 300 ml of acetic acid. Sodium nitrite (13.8 g, 0.2 mol) was added portionwise over 45 minutes while maintaining the temperature in the range 20°-30° C. After stirring for an additional 90 minutes at room temperature, the resulting yellow solution was stripped in vacuo to solids which were distributed between 300 ml each of water and ethyl acetate. The organic layer was separated, washed with saturated NaCl, dried over MgSO4 and stripped to yield 7.0 g of title product as a yellow oil, used directly in the next step; tlc Rf 0.08 (3:1 hexane:ethyl acetate).

Workup

  1. temperaturewhile maintaining the temperature in the range 20°-30° C
  2. customThe organic layer was separated
  3. washwashed with saturated NaCl
  4. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-596d391bf5a44fdf8a521b36fc4c4122
Source dataset
uspto-grants-1989_10
Patent number
US04874877

Reaction notes

Loading…