L-Glutamine → L-Glutamine, N2-[(phenylmethoxy)carbonyl]-
Reaction equation
[NH2:1][C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][C:5](=[O:7])[NH2:6].C([O-])([O-])=O.[Na+].[Na+].Cl[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19]>[OH-].[Na+].O1CCOCC1>[CH2:21]([O:20][C:18]([NH:1][C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][C:5](=[O:7])[NH2:6])=[O:19])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
Glutamine (1.84 g, 12.62 mmol) was dissolved in 1 N NaOH (12.58 mL) and the solution was cooled to 0° C. and stirred for 30 min, when Na2CO3 (3.30 g) and benzyl chloroformate (4.38 mL) in dioxane (19.30 mL) were gradually added, in equal portions. Stirring continued at 0° C. for 1 h, then the solution was allowed to stir overnight at room temperature and was extracted with ethyl ether (2×20 mL). The aqueous solution was acidified with 2N HCl to pH 5 and extracted with ethyl acetate (3×50 mL), which was dried over sodium sulfate, and evaporated to give an oil which crystallized overnight. Recrystallization of the crude product gave a white crystalline material (3.07 g, 87%); FABMS 319.1 (M+K), 281.1 (M+H).
Workup
- stirringStirring
- waitcontinued at 0° C. for 1 h
- stirringto stir overnight at room temperature
- extractionwas extracted with ethyl ether (2×20 mL)
- extractionextracted with ethyl acetate (3×50 mL), which
- dry with materialwas dried over sodium sulfate
- customevaporated
- customto give an oil which
- customcrystallized overnight
- customRecrystallization of the crude product
Sources & evidence
- ORD record
- ord-f893ed269d6f425989e38a2aa611e49b
- Source dataset
- uspto-grants-2005_01
- Patent number
- US06841530B2
Reaction notes
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