Sodium hydride → HCID 85933686, compound

HRID 1247001Notes

Reaction equation

HRID 1247001 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:10])[C@H:6]([CH3:9])[NH:7][CH3:8])[CH3:3].[H-].[Na+].[C:13]([S:16][CH2:17][CH2:18][C:19](Cl)=[O:20])(=[O:15])[CH3:14].C(=O)(O)[O-].[Na+]>O1CCCC1>[CH2:2]([O:4][C:5](=[O:10])[CH:6]([N:7]([C:19](=[O:20])[CH2:18][CH2:17][S:16][C:13](=[O:15])[CH3:14])[CH3:8])[CH3:9])[CH3:3]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 129431223-(Acetylsulfanyl)propanoyl chlorideHCID 86621252117856-39-0

Product 1

HCID 85933686HCID 85933686, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The solution of 15 g (89.5 mmol) of N-methylalanine ethyl ester-hydrochloride in 850 ml of anhydrous tetrahydrofuran is mixed at 23° C. with 4.1 g of an approximately 60% sodium hydride dispersion and, after 3 hours, with 23.5 g of 3-acetylsulfanyl-propanoic acid chloride. It is allowed to react for two days, mixed with saturated sodium bicarbonate solution, and extracted several times with ethyl acetate. The combined organic extracts are washed with saturated sodium chloride solution, dried over sodium sulfate, and the residue that is obtained after filtration and removal of the solvent is purified by chromatography on fine silica gel. 17.6 g (67.3 mmol, 75%) of the title compound is isolated as a colorless oil.

Workup

  1. customto react for two days
  2. extractionextracted several times with ethyl acetate
  3. washThe combined organic extracts are washed with saturated sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. customthe residue that is obtained
  6. filtrationafter filtration and removal of the solvent
  7. customis purified by chromatography on fine silica gel

Sources & evidence

ORD record
ord-911cb272c06e4a75b51a0d742a61c148
Source dataset
uspto-grants-2006_10
Patent number
US07129254B2

Reaction notes

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