tert-Butanol → HCID 90132491, 화합물

HRID 2275787노트

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HRID 2275787 반응식
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH:12]([C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)[CH2:13]C(O)=O.C(N(CC)CC)C.[N:31]12[CH2:38]CN(CC1)CC2.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:46])C=CC=CC=1.[C:56]([OH:60])([CH3:59])([CH3:58])[CH3:57]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH:12]([C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)[CH2:13][NH:31][C:38](=[O:46])[O:60][C:56]([CH3:59])([CH3:58])[CH3:57]

참가 물질

8

반응물 5

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 9237DabcoHCID 199401P,P-Diphenylphosphinic azideHCID 3816170HCID 3816170, 화합물

생성물 1

HCID 90132491HCID 90132491, 화합물

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

Under argon, a solution of 3.2 g of rac-3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-(4-fluorophenyl)propanoic acid (Example 47A, 8.78 mmol) in 32 ml of toluene was initially charged, and 1.33 g of triethylamine (13.18 mmol), 98 mg of 1,4-diazabicyclo[2.2.2]octane (0.88 mmol), 3.14 g of diphenylphosphoryl azide (11.42 mmol) and 6.51 g of tert-butanol (87.84 mmol) were added. The reaction mixture was heated at reflux overnight and then diluted with ethyl acetate and washed with water. The organic phase was dried over sodium sulphate, filtered and concentrated. The crude product was purified by silica gel chromatography (mobile phase: cyclohexane/ethyl acetate 8:1; 6:1). This gave 959 mg of the title compound (28% of theory).

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. washwashed with water
  4. dry with materialThe organic phase was dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by silica gel chromatography (mobile phase: cyclohexane/ethyl acetate 8:1; 6:1)

출처 및 근거

ORD 기록
ord-bebad59cf44442a883d375d9d7e67674
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09126998B2

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