Ethylene Glycol → HCID 23387517, compound

HRID 1790767Notes

Reaction equation

HRID 1790767 reaction equation
C1CCC(N=C=NC2CCCCC2)CC1.[CH2:16]([OH:19])[CH2:17][OH:18].[C:20]([NH:30][C@H:31]([C:35](O)=[O:36])[CH:32]([CH3:34])[CH3:33])([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:20]([NH:30][C@H:31]([C:35]([O:18][CH2:17][CH2:16][OH:19])=[O:36])[CH:32]([CH3:34])[CH3:33])([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21]

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 10868DicyclohexylcarbodiimideHCID 726987N-Carbobenzoxy-L-valine

Product 1

HCID 23387517HCID 23387517, compoundYield 81.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of DCC (11.4 g, 55 mmol), DMAP (0.611 g, 5 mmol) and ethyleneglycol (55.8 mL, 1 mol) in CH2Cl2 (300 mL) at 0° C., was added dropwise a solution of N-CBz-L-valine (12.6 g, 50 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, 5→10% MeOH in CH2Cl2), to give 12.0 g 2-(N-CBz-L-valyloxy)-ethanol.

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, 5→10% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-6f293788d4df43258d54eb833145349c
Source dataset
uspto-grants-2006_07
Patent number
US07071173B2

Reaction notes

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