Ethyl Acrylate → (+/-)-tert-Butyl 4-(1-(5-cyanobenzo[d]oxazol-2-yl)-4-ethoxy-4-oxobutyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate

HRID 2174121노트

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HRID 2174121 반응식
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([CH2:11][C:12]3[C:20]([O:21][CH3:22])=[CH:19][C:18]([CH3:23])=[C:17]4[C:13]=3[CH:14]=[CH:15][N:16]4[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[N:8][C:7]=2[CH:31]=1)#[N:2].CC(C)([O-])C.[K+].C1OCCOCCOCCOCCOCCOC1.[C:56]([O:60][CH2:61][CH3:62])(=[O:59])[CH:57]=[CH2:58].[Cl-].[NH4+]>C1COCC1>[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([CH:11]([C:12]3[C:20]([O:21][CH3:22])=[CH:19][C:18]([CH3:23])=[C:17]4[C:13]=3[CH:14]=[CH:15][N:16]4[C:24]([O:26][C:27]([CH3:28])([CH3:30])[CH3:29])=[O:25])[CH2:58][CH2:57][C:56]([O:60][CH2:61][CH3:62])=[O:59])=[N:8][C:7]=2[CH:31]=1)#[N:2]

참가 물질

7

반응물 5

HCID 8821Ethyl AcrylateHCID 25517Ammonium ChlorideHCID 2855718-Crown-6HCID 23665647Potassium tert-butoxideHCID 86701743tert-Butyl 4-((5-cyanobenzo[d]oxazol-2-yl)methyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate

생성물 1

HCID 86701763(+/-)-tert-Butyl 4-(1-(5-cyanobenzo[d]oxazol-2-yl)-4-ethoxy-4-oxobutyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매4회

실험 절차

A solution of tert-butyl 4-((5-cyanobenzo[d]oxazol-2-yl)methyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate (Example 144-A) (189 mg, 0.453 mmol) in THF (1.7 mL) was added to a solution of potassium tert-butoxide (50.8 mg, 0.453 mmol) in THF (1.7 mL) under nitrogen at −78° C. After stirring for 15 min a solution 18-crown-6 (11.97 mg, 0.045 mmol) in THF (566 μl) was added to the mixture at the same temperature and the reaction was then stirred for another 15 min. At this point ethyl acrylate (61.5 μl, 0.679 mmol) in THF (566 μl) was added dropwise. After 25 minutes, the reaction mixture was poured into a solution of saturated ammonium chloride, extracted with EtOAc (2×), passed through a phase separator and concentrated and purified via FCC with Heptane/AcOEt (100/0 to 70/30) to afford the title compound. MS (ESI+) m/z 418.4 (M+H-Boc).

후처리

  1. additionwas added to the mixture at the same temperature
  2. waitAfter 25 minutes
  3. extractionextracted with EtOAc (2×)
  4. concentrationconcentrated
  5. custompurified via FCC with Heptane/AcOEt (100/0 to 70/30)

출처 및 근거

ORD 기록
ord-2c43ad3a6a524bbda389970b50a67363
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09056874B2

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