Dichloromethane → (R)-3-pyrrolidin-3-yl-4H-1,2,4-oxadiazol-5-one

HRID 1040415노트

반응식

HRID 1040415 반응식
C(OC([N:8]1[CH2:12][CH2:11][C@@H:10]([C:13]2[NH:17][C:16](=[O:18])[O:15][N:14]=2)[CH2:9]1)=O)(C)(C)C.C(Cl)Cl.C1(S)C=CC=CC=1>C(O)(C(F)(F)F)=O>[NH:8]1[CH2:12][CH2:11][C@@H:10]([C:13]2[NH:17][C:16](=[O:18])[O:15][N:14]=2)[CH2:9]1

참가 물질

5

반응물 3

HCID 6344DichloromethaneHCID 7969ThiophenolHCID 136383477(R)-3-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 136383470(R)-3-pyrrolidin-3-yl-4H-1,2,4-oxadiazol-5-one수율 91.1%

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

실험 절차

Crude (R)-3-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester (872 mg, 3.41 mmol), CH2Cl2 (5 mL) and thiophenol (0.7 mL, 6.8 mmol) were combined and diluted with TFA (5 mL). After 24 h, the reaction was concentrated in vacuo. The residue was partitioned between CH2Cl2 and water. The layers were separated and the CH2Cl2 layer was extracted with water. The combined aqueous layers were concentrated in vacuo. Reverse phase HPLC purification yielded 482 mg of (R)-3-pyrrolidin-3-yl-4H-1,2,4-oxadiazol-5-one as a tan oil (˜50% pure) that was used without further purification.

후처리

  1. concentrationthe reaction was concentrated in vacuo
  2. customThe residue was partitioned between CH2Cl2 and water
  3. customThe layers were separated
  4. extractionthe CH2Cl2 layer was extracted with water
  5. concentrationThe combined aqueous layers were concentrated in vacuo
  6. customReverse phase HPLC purification

출처 및 근거

ORD 기록
ord-13e92986632d44e498977bc5e7910043
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08552205B2

반응 노트

불러오는 중…