Dicyclohexylcarbodiimide → HCID 54380268, compound

HRID 1790804Notes

Reaction equation

HRID 1790804 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].[CH3:34][O:35][C:36]1[CH:55]=[CH:54][C:39]([CH2:40][O:41][C:42]([C:44]2[CH:49]=[CH:48][C:47](=[O:50])[N:46]([CH2:51][CH2:52]O)[CH:45]=2)=[O:43])=[CH:38][CH:37]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:34][O:35][C:36]1[CH:37]=[CH:38][C:39]([CH2:40][O:41][C:42]([C:44]2[CH:49]=[CH:48][C:47](=[O:50])[N:46]([CH2:51][CH2:52][O:32][C:31](=[O:33])[C@H:27]([CH:28]([CH3:29])[CH3:30])[NH:26][C:16]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:17])[CH:45]=2)=[O:43])=[CH:54][CH:55]=1

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 726987N-Carbobenzoxy-L-valineHCID 54199935HCID 54199935, compound

Product 1

HCID 54380268HCID 54380268, compoundYield 52.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of DCC (5.06 g, 24.5 mmol), DMAP (318 mg, 2.6 mmol) and N-CBz-L-valine (6.48 g, 25.8 mmol) in CH2Cl2 (200 mL) at 0° C., was added dropwise a solution of 1-(2-hydroxyethyl)-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid 4-methoxybenzyl ester (6.40 g, 24 mmol) in CH2Cl2 (200 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 6.81 g 1-(2-N-CBz-L-valyloxyethyl)-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid 4-methoxybenzyl ester.

Workup

  1. customto assume room temperature
  2. filtrationThe mixture was filtered through a glass
  3. filtrationfilter
  4. customthe solvent was removed under reduced pressure
  5. customchromatographed (silica gel, 2→5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-1b392be574854eb89473495727cb5b14
Source dataset
uspto-grants-2006_07
Patent number
US07071173B2

Reaction notes

Loading…