L-Aspartic Acid → N-(Benzyloxycarbonyl)aspartic acid

HRID 1589438Notes

Reaction equation

HRID 1589438 reaction equation
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][C:4]([OH:6])=[O:5].[OH-].[Na+].Cl[C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14]>O>[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][C:4](=[O:6])[OH:5]

Participants

5

Reactant 3

HCID 5960L-Aspartic Acid2×HCID 10387Benzyl chloroformateHCID 14798Sodium Hydroxide2×

Product 1

HCID 2723942N-(Benzyloxycarbonyl)aspartic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In most cases the Z-Asp dialkali metal salt was prepared in a 1 liter multi-necked flask equipped with a reflux condenser, two dropping funnels, a thermometer, a pH probe and a mechanical stirrer. L-Aspartic acid and water were charged into the flask and a 25% NaOH solution was added with stirring until the L-aspartic acid was fully dissolved. Benzyl chloroformate was added to the reaction mixture with sufficient sodium hydroxide solution to maintain the reaction mixture within the desired pH range. After the reaction was completed, each reaction mixture was separated into two equal portions and the Z-Asp was isolated under the conditions set forth in TABLE I. The temperatures of the crystallizations were controlled as shown in TABLE I. The product analyses are also set forth.

Workup

  1. customequipped with a reflux condenser
  2. dissolutionwas fully dissolved
  3. temperatureto maintain the reaction mixture within the desired pH range
  4. customeach reaction mixture was separated into two equal portions

Sources & evidence

ORD record
ord-aa6a427deee844c8a0dc0997553dc326
Source dataset
uspto-grants-1986_02
Patent number
US04570015

Reaction notes

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