Benzyl chloroformate → (2R)-2-(((benzyloxy)carbonyl)amino)butanedioic acid

HRID 1440676

반응식

HRID 1440676 반응식
[NH2:1][C@@H:2]([C:7]([OH:9])=[O:8])[CH2:3][C:4]([OH:6])=[O:5].Cl[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12].[OH-].[Na+]>O>[CH2:14]([O:13][C:11]([NH:1][C@@H:2]([C:7]([OH:9])=[O:8])[CH2:3][C:4]([OH:6])=[O:5])=[O:12])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

참가 물질

5

반응물 3

HCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 83887D-Aspartic Acid

생성물 1

HCID 5289152(2R)-2-(((benzyloxy)carbonyl)amino)butanedioic acid

시약·촉매·용매 1

HCID 962Water용매

실험 절차

D-Aspartic acid (25.0 g, 0.188 mol) and benzyl chloroformate (34.3 ml, 0.282 mol) were added to sodium hydroxide (22.9 g, 0.564 mol) in water (600 ml). The resulting mixture was stirred at room temperature for 3 days. The mixture was then acidified with 6MHCl to pH1 and extracted with ethyl acetate (3×250 ml). The extracts were combined, dried (MgSO4) and evaporated to a clear oil, wt 50.2 g. 1H NMR (90 MHz, CDCl3): δ 3.05 (2,bm), 4.65 (1,bm), 5.25 (2,s), 6.2 (1,bs), 7.4 (5,s), 10 (1,bs).

후처리

  1. extractionextracted with ethyl acetate (3×250 ml)
  2. dry with materialdried (MgSO4)
  3. customevaporated to a clear oil, wt 50.2 g

출처 및 근거

ORD 기록
ord-936d166b05d4498faf771494cd57af04
출처 데이터셋
uspto-grants-1996_03
특허 번호
US05500419

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