Hydrochloric Acid → HCID 86757100, compound

HRID 1383725Notes

Reaction equation

HRID 1383725 reaction equation
CC(C)([O-])C.[K+].C([O:9][C:10](=[O:18])[CH2:11][N:12]=[C:13]([S:16][CH3:17])[S:14][CH3:15])C.[C:19]([C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH2:26]Br)([CH3:22])([CH3:21])[CH3:20].[OH-].[Na+].Cl>C1COCC1.O>[CH3:17][S:16][C:13]([S:14][CH3:15])=[N:12][C@H:11]([C:10]([OH:9])=[O:18])[CH2:26][C:25]1[CH:28]=[CH:29][CH:30]=[C:23]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:24]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10965701N-[BIS(METHYLTHIO)METHYLENE]GLYCINE ETHYL ESTERHCID 140976451-(Bromomethyl)-3-tert-butylbenzeneHCID 23665647Potassium tert-butoxide

Product 1

HCID 86757100HCID 86757100, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1.78 g (15.8 mmol) of potassium t-butoxide in 30 ml of THF, a solution of 3.28 g (15.8 mmol) of N-[bis(methylthio)methylene]glycine ethyl ester (Angew. Chem. Internat. Edit., 14, 426 (1975)) and 2.39 g (10.5 mmol) of 3-t-butylbenzyl bromide (Eur. J. Med. Chem., 23, 477 (1988)) in 10 ml of THF was added at −78° C. and the mixture was stirred at room temperature for 1 hour. Under cooling with ice, 10 ml of water was added, then 5 ml of 2 N aqueous sodium hydroxide was added and the mixture was stirred at room temperature for another 1 hour. Under cooling with ice, 2 N hydrochloric acid was added to the reaction mixture to render it acidic; the reaction mixture was extracted with chloroform and washed first with water, then with saturated brine. The organic layer was dried with anhydrous magnesium sulfate and concentrated under reduced pressure; the resulting residue was subjected to silica gel column chromatography (eluting solvent; ethyl acetate) to give N-[bis(methylthio)methylene]-3-t-butylphenylalanine in the amount of 577 mg (16%).

Workup

  1. additionwas added
  2. stirringthe mixture was stirred at room temperature for another 1 hour
  3. additionwas added to the reaction mixture
  4. extractionthe reaction mixture was extracted with chloroform
  5. washwashed first with water
  6. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. washthe resulting residue was subjected to silica gel column chromatography (eluting solvent; ethyl acetate)

Sources & evidence

ORD record
ord-fb1a641b321c43d0971293299e87732a
Source dataset
uspto-grants-2001_07
Patent number
US06255285B1

Reaction notes

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