Sodium Hydroxide → (R)-2-benzyloxycarbonylamino-2-ethoxycarbonylsuccinimide

HRID 1671701Notes

Reaction equation

HRID 1671701 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:17][C:16](=[O:18])[NH:15][C:13]1=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=O)CC(CC([O-])=O)(C([O-])=O)O.[OH-].[Na+].S([O-])([O-])(=O)=O.[NH4+].[NH4+]>CS(C)=O>[CH2:1]([O:8][C:9]([NH:11][C@:12]1([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:17][C:16](=[O:18])[NH:15][C:13]1=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 31348CitrateHCID 6097028Ammonium SulfateHCID 10267979Ethyl 3-(((benzyloxy)carbonyl)amino)-2,5-dioxopyrrolidine-3-carboxylate

Product 1

HCID 9944916(R)-2-benzyloxycarbonylamino-2-ethoxycarbonylsuccinimideYield 48%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

5.0 g of 2-benzyloxycarbonylamino-2-ethoxycarbonyl succinimide were dissolved in 100 g of dimethylsulfoxide and thereto, 100 g of 0.05 mol/L citrate buffer solution (pH 4.4) were added, followed by adjusting pH value of the resultant mixture to 6.5 with a 5% sodium hydroxide aqueous solution. Thereto, 0.28 mL of esterase (PLE (2.7 kU/mL); manufactured by BioCatalytics, Inc., ammonium sulfate suspension) were added and the resultant mixture was stirred at 25° C. for 78 hours, followed by analyzing quantitatively the reaction mixture. As a result, in the reaction mixture, 2.4 g (quantitative yield: 48.6%) of (R)-2-benzyloxycarbonylamino-2-ethoxycarbonyl succinimide having an optical purity of 97-5% e.e. were contained

Sources & evidence

ORD record
ord-1d3648cab4ec4799a02fa82aadd1515a
Source dataset
uspto-grants-2011_08
Patent number
US07994342B2

Reaction notes

Loading…