Dicyclohexylcarbodiimide → HCID 23387550, compound
Reaction equation
C1CCC(N=C=NC2CCCCC2)CC1.[OH:16][CH:17]([CH2:34][OH:35])[CH2:18][C:19]([CH3:33])([CH3:32])[C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=1)=[O:21].[C:36]([NH:46][C@H:47]([C:51](O)=[O:52])[CH:48]([CH3:50])[CH3:49])([O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:37]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:36]([NH:46][C@H:47]([C:51]([O:35][CH2:34][CH:17]([OH:16])[CH2:18][C:19]([CH3:32])([CH3:33])[C:20]([O:22][CH2:23][C:24]1[CH:25]=[CH:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=1)=[O:21])=[O:52])[CH:48]([CH3:50])[CH3:49])([O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:37]Participants
6
Procedure
To a mixture of DCC (14.8 g, 72 mmol), DMAP (0.88 g, 7.2 mmol) and 4-methoxybenzyl 4,5-dihydroxy-2,2-dimethyl-valerate (20.3 g, 72 mmol) in CH2Cl2 (400 mL) at 0° C., was added dropwise a solution of N-CBz-L-valine (16.2 g, 65 mmol) in CH2Cl2 (100 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 5 h 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, 2→5% MeOH in CH2Cl2), to give 22.4 g 4-methoxybenzyl 5-(N-CBz-L-valyloxy)-4-hydroxy-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, 2→5% MeOH in CH2Cl2)
Sources & evidence
- ORD record
- ord-5c74924108fa4208806b46644550275d
- Source dataset
- uspto-grants-2006_07
- Patent number
- US07071173B2
Reaction notes
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