Hydrochloric Acid → HCID 69931447, compound

HRID 2297699Notes

Reaction equation

HRID 2297699 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH:5]([CH2:13][S:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[NH:6][C:7](=O)[CH2:8][CH:9]([CH3:11])[CH3:10])[CH3:2].[ClH:22]>O1CCCC1.C(O)C>[ClH:22].[CH2:1]([O:3][C:4](=[O:21])[CH:5]([CH2:13][S:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[NH:6][CH2:7][CH2:8][CH:9]([CH3:11])[CH3:10])[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 22722884HCID 22722884, compound

Product 1

HCID 69931447HCID 69931447, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of N-isovaleryl-3-(phenylthio)-DL-alanine ethyl ester (1.0 g) in anhydrous tetrahydrofuran (3.2 ml) is added to a 1 M solution of a borane-tetrahydrofuran complex salt in tetrahydrofuran (4.85 ml) dropwise under a nitrogen atmosphere and ice cooling, and the mixture is refluxed with stirring for one hour. A 3 N solution of hydrogen chloride in ethanol (2 ml) is added to the reaction mixture under ice cooling, and the mixture is further refluxed for one hour. The reaction mixture is concentrated under reduced pressure, 5% sodium hydrogencarbonate is added to the concentrate, and the whole is extracted with ether. The organic layer is washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue is purified by silica gel column chromatography, and the resulting oily matter is dissolved in ether. A 4.6 N solution of hydrogen chloride in ethyl acetate is added thereto under ice cooling, and the resulting precipitate is filtered off to give 163 mg (15%) of the titled compound (Reference compound No. 5-1) as crystals.

Workup

  1. temperaturethe mixture is refluxed
  2. temperaturethe mixture is further refluxed for one hour
  3. concentrationThe reaction mixture is concentrated under reduced pressure, 5% sodium hydrogencarbonate
  4. additionis added to the concentrate
  5. extractionthe whole is extracted with ether
  6. washThe organic layer is washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue is purified by silica gel column chromatography
  10. dissolutionthe resulting oily matter is dissolved in ether
  11. additionA 4.6 N solution of hydrogen chloride in ethyl acetate is added
  12. filtrationunder ice cooling, and the resulting precipitate is filtered off

Sources & evidence

ORD record
ord-6720cc07267c4397b83004ebd8229ade
Source dataset
uspto-grants-2002_12
Patent number
US06492370B1

Reaction notes

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