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

HRID 1603236

반응식

HRID 1603236 반응식
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]

참가 물질

7

반응물 4

HCID 1118Sulfuric AcidHCID 8255Isobutylene2회HCID 312751,4-DioxaneHCID 85756345Rac-5-amino-2-propylpentanoic acid monohydrochloride

생성물 1

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

시약·촉매·용매 2

HCID 280Carbon Dioxide용매HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c970bddf08814fa9adc63421d9c4e6aa
출처 데이터셋
uspto-grants-1999_11
특허 번호
US05986094

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