ChemicalBook CAS DataBase List L-Homoserine

L-Homoserine synthesis

10synthesis methods

Product Name:L-Homoserine
CAS Number:672-15-1
Molecular formula:C4H9NO3
Molecular Weight:119.12

3493-11-6
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$119.00/500mg

672-15-1
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$5.00/100mg

Yield:672-15-1 92%

Reaction Conditions:

with water;sodium hydrogencarbonate pH=2 - 5;Reflux;

Steps:

3

(2S)-Methionine methylsulfonium iodide (9.4 g, 32.3 mmol) was dissolved in water (30 mL) in a three-necked round-bottom flask and heated to reflux. Sodium bicarbonate (2.71 g, 32.3 mmol) was dissolved in water (40 mL), placed in a dropping funnel and added dropwise to the reaction mixture until the pH of the solution rose to 5.0 (monitored using a VWR symphony SB20 pH meter). The reaction was allowed to proceed until the pH dropped to 2.0 (~ 15 min), whereupon base was added as previously described (addition over 6 h). The reaction mixture was then allowed to stir with heating at reflux for 12 h before being cooled, transferred to a 50 mL round-bottom flask and concentrated to give a clear oil. The oil was dissolved in water (5 mL) and ethanol (10 mL), and treated with acetone (150 mL) to produce a white precipitate that was collected by filtration. The precipitate was dissolved in water (20 mL) and freeze-dried, giving (S)-2-amino-4-hydroxybutyric acid (2S)-9 as a white solid (3.55 g, 92%). R_f = 0.73 (40% EtOH / H₂O); mp: 175- 177 ⁰C (EtOH / Et₂O) (Lit."^a mp: 182-183 ⁰C); [α]_D²⁰ -8.5 (c 1.0, H₂O) [Lit."^a [α]_D²⁰ -8.9 (c 2.0, H₂O)]; ¹H NMR (300 MHz, D₂O) δ 1.86-1 .93 (m, 1H, β- CAVH), 1.99-2.05 (m, 1H, β-CHAV), 3.63-3.67 (m, 2H, γ-CH₂) and 3.71 (dd, 1 H, J 7.5, 4.8, α-CH); ¹³C NMR (75 MHz, D₂O) δ 32.9 (CH₂), 54.1 (CH), 59.4 (CH₂), 175.2 (C=O); m/z (ESI) 120 (MH⁺, 100%) and 102 (1 ).