반응 #2122527

반응 방정식

SOCl2

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

MeOH

→

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

반응 조건

후처리

1. 1
   온도a cooled
2. 2
   기타the cooling bath was removed
3. 3
   기타Most of the volatile component was removed in vacuo
4. 4
   기타the residue was carefully partitioned between EtOAc (150 mL) and saturated NaHCO3 solution
5. 5
   추출The aqueous phase was extracted with EtOAc (150 mL, 2×)
6. 6
   건조the combined organic phase was dried (MgSO4)
7. 7
   여과filtered
8. 8
   농축concentrated in vacuo

실험 절차

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]+ C12H16NO4: 238.11; found 238.22.

출처