Sodium Hydroxide → 1-{4-[2-(2-Cyclopentyl-4,6-dioxo-tetrahydro-pyran-2-yl)-ethyl]-2-fluoro-phenyl}-cyclopropanecarbonitrile

HRID 1453047노트

반응식

HRID 1453047 반응식
[CH:1]1([C:6]([OH:31])([CH2:21][C:22]2[O:23]C(C)(C)[O:25][C:26](=O)[CH:27]=2)[CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3([C:18]#[N:19])[CH2:17][CH2:16]3)=[C:11]([F:20])[CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>>[CH:1]1([C:6]2([CH2:7][CH2:8][C:9]3[CH:14]=[CH:13][C:12]([C:15]4([C:18]#[N:19])[CH2:16][CH2:17]4)=[C:11]([F:20])[CH:10]=3)[CH2:21][C:22](=[O:23])[CH2:27][C:26](=[O:25])[O:31]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

3

반응물 2

HCID 14798Sodium HydroxideHCID 587625831-{4-[3-Cyclopentyl-4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-3-hydroxy-butyl]-2-fluoro-phenyl}-cyclopropanecarbonitrile

생성물 1

HCID 587627061-{4-[2-(2-Cyclopentyl-4,6-dioxo-tetrahydro-pyran-2-yl)-ethyl]-2-fluoro-phenyl}-cyclopropanecarbonitrile수율 47.3%

실험 절차

A solution of 1-{4-[3-Cyclopentyl-4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-3-hydroxy-butyl]-2-fluoro-phenyl}-cyclopropanecarbonitrile (0.9 g, 2.1 mmol) from Step 6 below in NaOH (0.3 M in MeOH, 21 mL, 6.3 mmol) was stirred at room temperature for 3 hours. The reaction was then quenched with 100 mL saturated NH4Cl and 5 mL 1 N HCl. To this solution was added 100 mL CH2Cl2 and the layers were separated. The aqueous layer was extracted with 2×100 mL CH2Cl2 and the organic layers were combined. After drying the organic with MgSO4, and filtering to remove the solids, the solvent was removed by rotary evaporation. The remaining oil was purified by flash chromatography to yield the desired product (0.367 g, 47%). 1H NMR (CDCl3) δ: 1.27-1.30 (m, 2H), 1.51-1.73 (m, 10H), 1.84-1.89 (m, 2H), 2.19 (p, J=8.08 Hz, 1H), 2.58-2.71 (m, 4H), 3.36 (d, J=4.04 Hz, 2H), 6.81-6.86 (m, 2H), 7.16-7.18 (m, 1H). MS (ESI): 368 (M−H).

후처리

  1. customThe reaction was then quenched with 100 mL saturated NH4Cl and 5 mL 1 N HCl
  2. additionTo this solution was added 100 mL CH2Cl2
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with 2×100 mL CH2Cl2
  5. dry with materialAfter drying the organic with MgSO4
  6. filtrationfiltering
  7. customto remove the solids
  8. customthe solvent was removed by rotary evaporation
  9. customThe remaining oil was purified by flash chromatography

출처 및 근거

ORD 기록
ord-4947f0552ca644809abdafc5671fef8d
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07473790B2

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