Sulfuric Acid → Rac-5-amino-2-propylpentanoic acid 1,1-dimethylethyl ester

HRID 1603236

反応式

HRID 1603236 の反応式
O1CCOCC1.OS(O)(=O)=O.Cl.[NH2:13][CH2:14][CH2:15][CH2:16][CH:17]([CH2:21][CH2:22][CH3:23])[C:18]([OH:20])=[O:19].[CH3:24][C:25](=[CH2:27])[CH3:26]>C(=O)=O.O>[CH3:24][C:25]([O:19][C:18](=[O:20])[CH:17]([CH2:21][CH2:22][CH3:23])[CH2:16][CH2:15][CH2:14][NH2:13])([CH3:27])[CH3:26]

参加物

7

反応物 4

HCID 1118Sulfuric AcidHCID 8255Isobutylene2 回HCID 312751,4-DioxaneHCID 85756345Rac-5-amino-2-propylpentanoic acid monohydrochloride

生成物 1

HCID 54566902Rac-5-amino-2-propylpentanoic acid 1,1-dimethylethyl ester収率 49%

試薬・触媒・溶媒 2

HCID 280Carbon Dioxide溶媒HCID 962Water溶媒

実験手順

To a cooled solution of 7 mL of dioxane was added 0.7 mL of conc. H2SO4 dropwise. The solution turned purple in color. To this solution, 700 mg (3.5 mmol) of 5-amino-2-propylpentanoic acid monohydrochloride (7) was slowly added and the resulting solution was transferred into a pressure bottle. To this solution was added 12 mL of isobutylene and the resulting solution was slowly stirred magnetically under pressure at room temperature for 20 hours. The reaction vessel was cooled in dry ice, pressure was released, and the reaction vessel warmed up to room temperature to vaporize the excess isobutylene. The reaction mixture was poured into 100 mL of cold water. The aqueous part was extracted with 2×150 mL of ether, basified with 4N sodium hydroxide to pH 10, and extracted with 3×100 mL of ethyl acetate to yield 380 mg (1.76 mmol, 49%) of rac-5-amino-2-propylpentanoic acid 1,1-dimethylethyl ester (8) as an oil. NMR, IR and MS data confirmed the compound identity.

後処理

  1. temperaturethe reaction vessel warmed up to room temperature
  2. extractionThe aqueous part was extracted with 2×150 mL of ether
  3. extractionextracted with 3×100 mL of ethyl acetate

出典と根拠

ORDレコード
ord-c970bddf08814fa9adc63421d9c4e6aa
出典データセット
uspto-grants-1999_11
特許番号
US05986094

関連ノート

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