反応 #1772030

反応方程式

SOCl2

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

MeOH

→

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

反応条件

後処理

1. 1
   温度a cooled
2. 2
   その他the cooling bath was removed
3. 3
   その他Most of the volatile component was removed in vacuo
4. 4
   その他the residue was carefully partitioned between EtOAc (150 mL) and saturated NaHCO3 solution
5. 5
   抽出The aqueous phase was extracted with EtOAc (150 mL, 2×)
6. 6
   乾燥the combined organic phase was dried (MgSO4)
7. 7
   ろ過filtered
8. 8
   濃縮concentrated in vacuo

実験手順

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.

出典