Dicyclohexylcarbodiimide → 4-methoxybenzyl 5(N-CBz-L-valyloxy)-2,2-dimethylvalerate
Reaction equation
C1CCC(N=C=NC2CCCCC2)CC1.[C:16]([NH:26][C@H:27]([C:31]([OH:33])=[O:32])[CH:28]([CH3:30])[CH3:29])([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17].O[CH2:35][CH2:36][CH2:37][C:38]([CH3:52])([CH3:51])[C:39]([O:41][CH2:42][C:43]1[CH:48]=[CH:47][C:46]([O:49][CH3:50])=[CH:45][CH:44]=1)=[O:40]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:16]([NH:26][C@H:27]([C:31]([O:33][CH2:35][CH2:36][CH2:37][C:38]([CH3:51])([CH3:52])[C:39]([O:41][CH2:42][C:43]1[CH:48]=[CH:47][C:46]([O:49][CH3:50])=[CH:45][CH:44]=1)=[O:40])=[O:32])[CH:28]([CH3:29])[CH3:30])([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a mixture of DCC (9.41 g, 46 mmol), DMAP (0.586 g, 4.8 mmol) and N-CBz-L-valine (12.1 g, 48 mmol) in CH2Cl2 (200 mL) at 0° C., was added dropwise a solution of 4-methoxybenzyl 5-hydroxy-2,2-dimethyl-valerate (6.40 g, 24 mmol) in CH2Cl2 (50 mL). After 1 h at 0° C., the temperature of the reaction mixture was allowed to assume room temperature and then the mixture was stirred for 5h at room temperature. The mixture was filtered through a glass filter and the solvent was removed under reduced pressure. The crude product was column chromatographed (silica gel, 1→4% MeOH in CH2Cl2), to give 8.61 g 4-methoxybenzyl 5-(N-CBz-L-valyloxy)-2,2-dimethylvalerate.
Workup
- customto assume room temperature
- filtrationThe mixture was filtered through a glass
- filtrationfilter
- customthe solvent was removed under reduced pressure
- customchromatographed (silica gel, 1→4% MeOH in CH2Cl2)
Sources & evidence
- ORD record
- ord-501b24b0ffcc49809b8cd703a2f1cfef
- Source dataset
- uspto-grants-2002_10
- Patent number
- US06458772B1
Reaction notes
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