Ethanol → beta-Hydroxy Leucine ethyl ester hydrochloride

HRID 1256925

反応式

HRID 1256925 の反応式
S(Cl)([Cl:3])=O.[OH:5][CH:6]([CH:12]([CH3:14])[CH3:13])[C@@H:7]([C:9]([OH:11])=[O:10])[NH2:8].[CH2:15](O)[CH3:16]>>[ClH:3].[CH2:15]([O:10][C:9](=[O:11])[C@H:7]([CH:6]([OH:5])[CH:12]([CH3:14])[CH3:13])[NH2:8])[CH3:16]

参加物

4

反応物 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 134611Leucine, 3-hydroxy-

生成物 1

HCID 86659205beta-Hydroxy Leucine ethyl ester hydrochloride

実験手順

Into a 100 mL round-bottomed flask equipped with reflux condenser is added 50 mL ethanol and stirred using magnetic stirrer under positive nitrogen pressure. The flask is cooled using a dry ice/IPA bath to −35° C. Using an addition funnel 8.5 mL (0.12 mol) of thionyl chloride is added over 10 min. To the flask is then added 14.7 g (0.1 mol) of β-Hydroxy Leucine. The cooling bath is then removed and the flask heated using a heating mantle to reflux for 10 h. The reaction mixture is concentrated to 20 mL and then precipitated by adding 50 mL of ether. The product is isolated by filtration and washed with ether. The product β-Hydroxy Leucine ethyl ester hydrochloride is characterized by proton NMR and elemental analysis.

後処理

  1. customInto a 100 mL round-bottomed flask equipped
  2. temperaturewith reflux condenser
  3. temperatureThe flask is cooled
  4. customto −35° C
  5. additionis added over 10 min
  6. customThe cooling bath is then removed
  7. temperaturethe flask heated
  8. temperatureto reflux for 10 h
  9. concentrationThe reaction mixture is concentrated to 20 mL
  10. customprecipitated
  11. additionby adding 50 mL of ether
  12. customThe product is isolated by filtration
  13. washwashed with ether

出典と根拠

ORDレコード
ord-d4e51c5c25f54a91bd31acec589519fd
出典データセット
uspto-grants-2013_06
特許番号
US08461289B2

関連ノート

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