Hydrogen Bromide → L-Methionine

HRID 2221380Notes

Reaction equation

HRID 2221380 reaction equation
Br.[NH2:2][C@H:3]([C:7]([OH:9])=[O:8])[CH2:4][CH2:5]O.[Al+3].[Cl-].[Cl-].[Cl-].[CH:14]([SH:17])(C)C>>[NH2:2][C@H:3]([C:7]([OH:9])=[O:8])[CH2:4][CH2:5][S:17][CH3:14]

Participants

5

Reactant 4

HCID 260Hydrogen BromideHCID 63642-PropanethiolHCID 12647L-HomoserineHCID 6451240Aluminum(III) Chloride

Product 1

HCID 6137L-Methionine

Procedure

iPrSH (20 ml) was treated slowly with gaseous HBr. Subsequently L-homoserine (10 mmol) was added and the mixture was stirred for 10 minutes. Thereafter, AlCl3 (40 mmol) was added and the reaction mixture was stirred for 4 h at room temperature. The reaction mixture was quenched using H2O/HCl and then made basic with NaOH. After filtering off Al(OH)3 by suction the filtrate solution was concentrated to dryness and analysed by HPLC. Yield of (1)=8.2%. Activation of L-homoserine at the C-4 atom and reaction to give L-methionine

Workup

  1. stirringthe reaction mixture was stirred for 4 h at room temperature
  2. customThe reaction mixture was quenched
  3. filtrationAfter filtering off Al(OH)3 by suction the filtrate solution
  4. concentrationwas concentrated to dryness and analysed by HPLC
  5. customActivation of L-homoserine at the C-4 atom and reaction

Sources & evidence

ORD record
ord-bcd8693689fd46a7a952a722f8dc0558
Source dataset
uspto-grants-2008_05
Patent number
US07368600B2

Reaction notes

Loading…