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

HRID 1440676Notes

Reaction equation

HRID 1440676 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-936d166b05d4498faf771494cd57af04
Source dataset
uspto-grants-1996_03
Patent number
US05500419

Reaction notes

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