Benzyl Alcohol → HCID 6942172, compound

HRID 355436Notes

Reaction equation

HRID 355436 reaction equation
[NH2:1][C@@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].[CH2:10](O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[CH2:10]([O:8][C:7](=[O:9])[C@@H:2]([CH2:3][CH:4]([CH3:6])[CH3:5])[NH2:1])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

3

Reactant 2

HCID 244Benzyl AlcoholHCID 439524D-Leucine

Product 1

HCID 6942172HCID 6942172, compound

Conditions

Temperature
55 °C

Procedure

D-leucine (10 g, 76.23 mmol) is suspended in benzyl alcohol (157 mL) and warmed to 55° C. HCl gas is bubbled through the mixture and the reaction becomes quite viscous. 150 mL of benzene is then added with vigorous stirring. After 30 minutes of bubbling gas through with heating the mixture begins to thin and stirring is achieved more easily. The reaction stirs further at 55° C. for one hour until the solution becomes homogeneous. Flow of HCl is ceased and the reaction is closed off and allowed to stir further at 55° C. for 30 minutes. The reaction is allowed to cool to room temperature and is diluted with ethyl acetate. The product is extracted into 1M HCl (3×) and the organics are discarded. The aqueous washings are combined taken to pH 8 with 50% aqueous NaOH. The amine is extracted several times with ethyl acetate. The organics are dried over sodium sulfate and evaporated. Ether is added to the oil and HCl is bubbled through to precipitate D-leucine benzyl ester as the hydrochloride salt.

Workup

  1. customHCl gas is bubbled through the mixture
  2. addition150 mL of benzene is then added with vigorous stirring
  3. customAfter 30 minutes of bubbling gas through
  4. temperaturewith heating the mixture
  5. customthe reaction is closed off
  6. stirringto stir further at 55° C. for 30 minutes
  7. temperatureto cool to room temperature
  8. additionis diluted with ethyl acetate
  9. extractionThe product is extracted into 1M HCl (3×)
  10. extractionThe amine is extracted several times with ethyl acetate
  11. dry with materialThe organics are dried over sodium sulfate
  12. customevaporated
  13. additionEther is added to the oil and HCl
  14. customis bubbled through
  15. customto precipitate D-leucine benzyl ester as the hydrochloride salt

Sources & evidence

ORD record
ord-02be088e040242628cdb62572ede5e73
Source dataset
uspto-grants-1998_11
Patent number
US05830915

Reaction notes

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