3-Methyl-DL-aspartic acid → N-benzyloxycarbonyl-3-methyl-D,L-aspartic acid

HRID 1735696

Reaction equation

HRID 1735696 reaction equation
[CH3:1][CH:2]([C:8]([OH:10])=[O:9])[CH:3]([C:5]([OH:7])=[O:6])[NH2:4].Cl[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13].[OH-].[Na+]>O>[CH2:15]([O:14][C:12]([NH:4][CH:3]([C:5]([OH:7])=[O:6])[CH:2]([CH3:1])[C:8]([OH:10])=[O:9])=[O:13])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 8523-Methyl-DL-aspartic acidHCID 10387Benzyl chloroformateHCID 14798Sodium Hydroxide

Product 1

HCID 290744N-benzyloxycarbonyl-3-methyl-D,L-aspartic acidYield 100.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Using a similar method to above 3-methyl-D,L-aspartic acid (10.0 g, 67 mmol), benzyl chloroformate (12 ml, 100 mmol) in 50% NaOH (16.7 g, 208 mmol) in water (125 ml) yielded N-benzyloxycarbonyl-3-methyl-D,L-aspartic acid 19.0 g as a low melting solid. 1H NMR (90 MHz, CDCl3 /d6DMSO): δ1.1 (3,d), 2.9 (1,dt), 4.4 (1,m), 4.95 (2,s) 5.9 (1,bd) 7.2 (5,6) 7.9 (1,bs).

Sources & evidence

ORD record
ord-1fe87d433ab44cc1a2efbcfb451475fe
Source dataset
uspto-grants-1996_07
Patent number
US05538958

Linked notes

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