Hydrochloric Acid → 1-[(RS)-1-Cyano-[(S)-1-phenylpropylamino]methyl]-1-ethoxycarbonylcyclopropane

HRID 342047

반응식

HRID 342047 반응식
[C-:1]#[N:2].[K+].[C:4]1([C@@H:10]([NH2:13])[CH2:11][CH3:12])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH:14]([C:16]1([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:18][CH2:17]1)=O.Cl>C(O)C.O>[C:1]([CH:14]([NH:13][C@H:10]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH2:11][CH3:12])[C:16]1([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:18][CH2:17]1)#[N:2]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 9032Potassium CyanideHCID 6993773(1S)-1-phenylpropan-1-amineHCID 9964122Ethyl 1-formylcyclopropanecarboxylate

생성물 1

HCID 702112091-[(RS)-1-Cyano-[(S)-1-phenylpropylamino]methyl]-1-ethoxycarbonylcyclopropane수율 59.1%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

An eggplant type flask was charged with 136 mg of potassium cyanide, 501 mg of (S)-1-phenylpropylamine and 1 ml of water. After adding 152 mg of ethyl 1-formylcyclopropane-1-carboxylate dissolved in 2 ml of ethanol, dropwise at room temperature, the resulting mixture was further mixed with 0.2 ml of concentrated hydrochloric acid, and stirred for 1 hour at the same temperature and then for 2 hours at 50° C. After confirming completion of the reaction, the reaction solution was mixed with ice water and extracted with ethyl acetate. Next, the resulting organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate and, after removing insoluble matter by filtration, the solvent was evaporated under a reduced pressure. Thereafter, the resulting residue was subjected to a silica gel column chromatography (hexane:ethyl acetate=10:1) to obtain 181 mg (59%) of a diastereomer mixture in the form of colorless oil. Formation ratio of the two diastereomers was calculated under the following analytical conditions.

후처리

  1. waitfor 2 hours at 50° C
  2. customcompletion of the reaction
  3. extractionextracted with ethyl acetate
  4. washNext, the resulting organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customafter removing insoluble matter
  7. filtrationby filtration
  8. customthe solvent was evaporated under a reduced pressure

출처 및 근거

ORD 기록
ord-d5a95cc5e12c49ebb314619c0387ebd4
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05856518

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