Citric Acid → BOC-L-proline L-glutamic acid dibenzyl ester
Reaction equation
[C:1]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([OH:12])=[O:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(CC)CC)C.ClC(OCC)=O.[CH2:29]([O:36][C:37](=[O:52])[C@H:38]([CH2:40][CH2:41][C:42]([O:44][CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)=[O:43])[NH2:39])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>ClCCl.C(=O)(O)[O-].[Na+]>[C:1]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([OH:12])=[O:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH2:29]([O:36][C:37](=[O:52])[C@H:38]([CH2:40][CH2:41][C:42]([O:44][CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)=[O:43])[NH2:39])[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1Participants
8
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a solution of BOC-proline (Anderson G W and McGregor A C: J. Amer. Chem. Soc.: 79, 6810, 1994) (10 mmol) in dichloromethane (50 ml), cooled to 0° C., was added triethylamine (1.39 ml, 10 mmol) and ethyl chloroformate (0.96 ml, 10 mmol). The resultant mixture was stirred at 0° C. for 30 minutes. A solution of dibenzyl-L-glutamate (10 mmol) was then added and the mixture stirred at 0° C. for 2 hours then warmed to room temperature and stirred overnight. The reaction mixture was washed with aqueous sodium bicarbonate and citric acid (2 mol 1-1) then dried (MgSO4) and concentrated at reduced pressure to give BOC-L-proline-L-glutamic acid dibenzyl ester (5.0 g, 95%).
Workup
- temperaturethen warmed to room temperature
- stirringstirred overnight
- dry with materialthen dried (MgSO4)
- concentrationconcentrated at reduced pressure
Sources & evidence
- ORD record
- ord-27c4927a2e6b4e8cace9257fe01202e1
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07714020B2
Reaction notes
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