Potassium tert-butoxide → HCID 178487799, 화합물

HRID 1422942노트

반응식

HRID 1422942 반응식
CC(C)([O-:4])C.[K+].[C:7]([O:11][C:12](=[O:36])[NH:13][C@H:14]1[CH2:19][CH2:18][C@H:17]([CH:20]2[CH2:33][C:32]3[C:31]4[C:26](=[CH:27][CH:28]=[C:29]([O:34][CH3:35])[CH:30]=4)[N:25]=[CH:24][C:23]=3[O:22][CH2:21]2)[CH2:16][CH2:15]1)([CH3:10])([CH3:9])[CH3:8]>CS(C)=O.C(O)(C)(C)C>[C:7]([O:11][C:12](=[O:36])[NH:13][C@H:14]1[CH2:15][CH2:16][C@H:17]([CH:20]2[CH:33]([OH:4])[C:32]3[C:31]4[C:26](=[CH:27][CH:28]=[C:29]([O:34][CH3:35])[CH:30]=4)[N:25]=[CH:24][C:23]=3[O:22][CH2:21]2)[CH2:18][CH2:19]1)([CH3:10])([CH3:9])[CH3:8]

참가 물질

5

반응물 2

HCID 23665647Potassium tert-butoxideHCID 178487793HCID 178487793, 화합물

생성물 1

HCID 178487799HCID 178487799, 화합물

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 6386tert-Butanol용매

실험 절차

Potassium tert-butoxide (354 mg, 3.15 mmol, 2.5 eq) is added at room temperature to a stirred solution of [trans-4-(6-methoxy-3,4-dihydro-2H-1-oxa-9-aza-phenanthren-3-yl)-cyclohexyl]-carbamic acid tert-butyl ester (2.6 g, 1.26 mmol, 1.0 eq) in dimethyl sulfoxide (45 mL) and tert-butanol (13 mL) under oxygen atmosphere. After 1 hour stirring under oxygen atmosphere, the reaction mixture is purged with nitrogen, and extracted with dichloromethane (3×200 mL) and water (200 mL). The combined organic layers are dried over sodium sulfate, filtered and concentrated to give a residue that is purified by column chromatography (silica gel, eluent: dichloromethane:methanol, 250:1 to 100:1, v/v) to afford [trans-4-(4-hydroxy-6-methoxy-3,4-dihydro-2H-1-oxa-9-aza-phenanthren-3-yl)-cyclohexyl]-carbamic acid tert-butyl ester as a white solid that is further purified by preparative HPLC to obtain a white solid (70 mg, 42% yield).

후처리

  1. customthe reaction mixture is purged with nitrogen
  2. extractionextracted with dichloromethane (3×200 mL) and water (200 mL)
  3. dry with materialThe combined organic layers are dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a residue that
  7. customis purified by column chromatography (silica gel, eluent

출처 및 근거

ORD 기록
ord-4170daf818294bae8f824922cec8e345
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08927541B2

반응 노트

불러오는 중…