Reaktion #1772030

Reaktionsgleichung

SOCl2

(S)-3-amino-4-(benzyloxy)-4-oxobutanoic acid

MeOH

→

(S)-1-benzyl 4-methyl 2-aminosuccinate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperatura cooled
2. 2
   Sonstigethe cooling bath was removed
3. 3
   SonstigeMost of the volatile component was removed in vacuo
4. 4
   Sonstigethe residue was carefully partitioned between EtOAc (150 mL) and saturated NaHCO3 solution
5. 5
   ExtraktionThe aqueous phase was extracted with EtOAc (150 mL, 2×)
6. 6
   Trocknenthe combined organic phase was dried (MgSO4)
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated in vacuo

Vorschrift

SOCl2 (6.60 mL, 90.5 mmol) was added drop-wise over 15 min to a cooled (ice-water) mixture of (S)-3-amino-4-(benzyloxy)-4-oxobutanoic acid (10.04 g, 44.98 mmol) and MeOH (300 mL), the cooling bath was removed and the reaction mixture was stirred at ambient condition for 29 hr. Most of the volatile component was removed in vacuo and the residue was carefully partitioned between EtOAc (150 mL) and saturated NaHCO3 solution. The aqueous phase was extracted with EtOAc (150 mL, 2×), and the combined organic phase was dried (MgSO4), filtered, and concentrated in vacuo to afford (S)-1-benzyl 4-methyl 2-aminosuccinate as a colorless oil (9.706 g). 1H NMR (DMSO-d6, δ=2.5 ppm, 400 MHz): δ 7.40-7.32 (m, 5H), 5.11 (s, 2H), 3.72 (app t, J=6.6, 1H), 3.55 (s, 3H), 2.68 (dd, J=15.9, 6.3, 1H), 2.58 (dd, J=15.9, 6.8, 1H), 1.96 (s, 2H). LC (Cond. 1): RT=0.90 min; LC/MS: Anal. Calcd. for [M+H]+ Cl2H16NO4: 238.11. found 238.22.

Quelle