Sodium hydride → HCID 22940770, compound

HRID 1418787

Reaction equation

HRID 1418787 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C@H:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1)[NH:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7].[H-].[Na+].Br[CH2:28][CH2:29][O:30][CH2:31][CH2:32][O:33][CH3:34].C(=O)(O)[O-].[Na+]>CN(C)C=O.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:24])[C@H:4]([CH2:16][C:17]1[CH:18]=[CH:19][C:20]([O:23][CH2:28][CH2:29][O:30][CH2:31][CH2:32][O:33][CH3:34])=[CH:21][CH:22]=1)[NH:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 1235321-Bromo-3,6-dioxaheptaneHCID 516892Sodium BicarbonateHCID 7010613N-[(Phenylmethoxy)carbonyl]-L-tyrosine methyl ester

Product 1

HCID 22940770HCID 22940770, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

6.59 g (20 mmol) of N-benzyloxycarbonyl-tyrosine-methyl ester is dissolved in 25 ml of anhydrous N,N-dimethylformamide and mixed at 0° C. under argon with 0.81 g (20.5 mmol) of sodium hydride dispersion (60% in mineral oil). The batch is allowed to stir for 10 minutes, then 3.75 g (20.5 mmol) of 1-bromo-2-(2-methoxyethoxy)-ethane is added, the reaction temperature is allowed to increase to room temperature and stirred for another three hours. For working-up, the batch is taken up in toluene and shaken out several times against aqueous sodium bicarbonate solution. The organic phase is separated, dried on magnesium sulfate, filtered and concentrated by evaporation. The oily residue is chromatographed for purification on silica gel with hexane/diethyl ether/triethylamine.

Workup

  1. stirringstirred for another three hours
  2. customThe organic phase is separated
  3. customdried on magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated by evaporation
  6. customThe oily residue is chromatographed for purification on silica gel with hexane/diethyl ether/triethylamine

Sources & evidence

ORD record
ord-1341ac2f27f648288d7130e58f5f5e93
Source dataset
uspto-grants-1999_03
Patent number
US05885548

Linked notes

Loading…