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

HRID 1440676

反応式

HRID 1440676 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-936d166b05d4498faf771494cd57af04
出典データセット
uspto-grants-1996_03
特許番号
US05500419

関連ノート

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