2-Methyl-2-butene → HCID 86698614, 화합물

HRID 338267노트

반응식

HRID 338267 반응식
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]=[O:12])=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:13]1[CH:18]=[CH:17][C:16]([CH:19]2[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20]2)=[CH:15][CH:14]=1.CC(=CC)C.Cl([O-])=[O:37].[Na+].O.O.OP([O-])(O)=O.[Na+]>C(#N)C.C(O)(C)(C)C.O>[C:27]([O:26][C:24]([N:21]1[CH2:22][CH2:23][CH:19]([C:16]2[CH:17]=[CH:18][C:13]([C:3]3[CH:4]=[C:5]4[C:9](=[CH:10][C:2]=3[Cl:1])[NH:8][CH:7]=[C:6]4[C:11]([OH:37])=[O:12])=[CH:14][CH:15]=2)[CH2:20]1)=[O:25])([CH3:30])([CH3:29])[CH3:28]

참가 물질

8

반응물 4

HCID 105532-Methyl-2-buteneHCID 23668197Sodium Chlorite2회HCID 23673460Sodium Phosphate, Monobasic, Dihydrate2회HCID 86698613HCID 86698613, 화합물

생성물 1

HCID 86698614HCID 86698614, 화합물수율 36.3%

시약·촉매·용매 3

HCID 962Water용매2회HCID 6342Acetonitrile용매HCID 6386tert-Butanol용매

반응 조건

온도
0 °C

실험 절차

To a solution of tert-butyl 3-[4-(6-chloro-3-formyl-1H-indol-5-yl)phenyl]pyrrolidine-1-carboxylate (43 mg, 0.1 mmol) in acetonitrile (1.2 mL) and tert-butanol (1.2 mL) was added 2-methyl-2-butene (1.2 mL). The reaction mixture was cooled to 0° C. and treated with a solution of sodium chlorite (100 mg, 1.1 mmol) and sodium phosphate monobasic dihydrate (234 mg, 1.5 mmol) in water (0.6 mL). After the resulting mixture was stirred for 2 h at room temperature, additional sodium chlorite (134 mg, 1.47 mmol) and sodium phosphate monobasic dihydrate (312 mg, 2.0 mmol) in H2O (0.6 mL) was added to the reaction mixture. The resulting mixture was stirred at room temperature for 16 h. The reaction mixture was concentrated in vacuo and the aqueous residue was extracted with EtOAc (3×20 mL). The combined organic layers were dried over Na2SO4 and concentrated in vacuo. The residue was dissolved in DMSO and purified via pre-HPLC to give 5-{4-[1-(tert-butoxycarbonyl)pyrrolidin-3-yl]phenyl}-6-chloro-1H-indole-3-carboxylic acid (16 mg, 36%) as a white solid. MS (ES+) 463.1 (M+Na)+.

후처리

  1. stirringThe resulting mixture was stirred at room temperature for 16 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. extractionthe aqueous residue was extracted with EtOAc (3×20 mL)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue was dissolved in DMSO
  7. custompurified via pre-HPLC

출처 및 근거

ORD 기록
ord-98861d3dd7a7405b8462918843a19a90
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889730B2

반응 노트

불러오는 중…