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

HRID 1728308

Reaction equation

HRID 1728308 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-7f892152271b4d709277c712b0bf43c3
Source dataset
uspto-grants-1994_07
Patent number
US05326756

Linked notes

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