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(1R,2S)-Tranylcypromine → HCID 58842375, 화합물

HRID 1270443
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HRID 1270443 반응식
[CH2:1]1[C@@H:3]([NH2:4])[C@@H:2]1[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[N:11]([CH:14]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]([O:17]CC)=O)=[C:12]=[O:13]>ClCCl>[CH2:20]([CH:14]1[NH:11][C:12](=[O:13])[N:4]([CH2:3][C:2]2([C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH2:1][CH2:5][CH2:2][CH2:1][CH2:3]2)[C:15]1=[O:17])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 19493(1R,2S)-TranylcypromineHCID 12370705Ethyl N-(oxomethylidene)phenylalaninate

생성물 1

HCID 58842375HCID 58842375, 화합물수율 38.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of compound 1 (0.255 g; 1.35 mmol) in anhydrous dichloromethane (8 mL) was treated with ethyl 2-isocyanato-3-phenylpropionate (0.325 g; 0.38 mmol) and stirred at room temperature overnight. The solvent was removed by evaporation, the residue was dissolved in ethanol (1 mL), 6N hydrochloric acid (0.5 mL) and water (0.5 mL) and the reaction mixture was heated to 50° C. After 3 h at 50° C., additional 6N hydrochloric acid (1 mL) was added and the reaction mixture was heated at 65° C. overnight. The reaction mixture was concentrated and the crude product was purified directly by column chromatography on silica gel using 1:1 ethyl acetate:hexane as the eluent to give 0.053 g of 5-Benzyl-3-(1-phenyl-cyclohexylmethyl)-imidazolidine-2,4-dione as a white solid. Mass Spec [M+H]+=363.

후처리

  1. customThe solvent was removed by evaporation
  2. dissolutionthe residue was dissolved in ethanol (1 mL)
  3. temperature6N hydrochloric acid (0.5 mL) and water (0.5 mL) and the reaction mixture was heated to 50° C
  4. waitAfter 3 h at 50° C.
  5. additionadditional 6N hydrochloric acid (1 mL) was added
  6. temperaturethe reaction mixture was heated at 65° C. overnight
  7. concentrationThe reaction mixture was concentrated
  8. customthe crude product was purified directly by column chromatography on silica gel using 1:1 ethyl acetate

출처 및 근거

ORD 기록
ord-8ca88ec8d5c94c61bb35106fd54c435b
출처 데이터셋
uspto-grants-2007_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07202253B2

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