Sodium Hydroxide → HCID 123978986, 화합물

HRID 60655

반응식

HRID 60655 반응식
[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[CH:9][C:10]([O:15][Si:16]([CH:23]([CH3:25])[CH3:24])([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:19])[CH3:18])=[C:11]([CH2:13][OH:14])[CH:12]=2)[N:5]=[C:4]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH:3]=1.[OH-].[Na+].[Cl:32][C:33]([Cl:40])([Cl:39])[CH2:34][O:35][C:36](Cl)=[O:37]>CCOC(C)=O.O>[Cl:32][C:33]([Cl:40])([Cl:39])[CH2:34][O:35][C:36](=[O:37])[NH:1][C:2]1[N:6]([C:7]2[CH:8]=[CH:9][C:10]([O:15][Si:16]([CH:20]([CH3:21])[CH3:22])([CH:23]([CH3:25])[CH3:24])[CH:17]([CH3:18])[CH3:19])=[C:11]([CH2:13][OH:14])[CH:12]=2)[N:5]=[C:4]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH:3]=1

참가 물질

6

반응물 3

HCID 14798Sodium Hydroxide2회HCID 870632,2,2-Trichloroethyl chloroformate2회HCID 123490636[5-(5-Amino-3-tert-butyl-pyrazol-1-yl)-2-triisopropylsilanyloxy-phenyl]-methanol

생성물 1

HCID 123978986HCID 123978986, 화합물수율 84%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매2회

실험 절차

To a solution of Intermediate 61c (0.15 g, 0.36 mmol) in EtOAc (1.8 mL) was added 1N aqueous NaOH solution (0.6 mL, 0.60 mmol) followed by 2,2,2-trichloroethylchloroformate (54.0 μL, 0.40 mmol). The reaction was stirred at RT overnight then treated with another portion of 1N aqueous NaOH solution (0.3 mL, 0.30 mmol) followed by 2,2,2-trichloroethylchloroformate (27.0 μL, 0.20 mmol). After stirring for another 4 h, the mixture was diluted with EtOAc and water. The aqueous layer was then extracted with EtOAc (2×). The combined organic layers were washed with brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified by FCC, using 0-25% EtOAc in cyclohexane, to give the title compound (176 mg, 84%). LCMS (Method 3): Rt 5.35 min, m/z 592, 594 [MH+].

후처리

  1. stirringAfter stirring for another 4 h
  2. extractionThe aqueous layer was then extracted with EtOAc (2×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was purified by FCC

출처 및 근거

ORD 기록
ord-aa1b9967686a4a40bc02b8814a2e7f36
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440974B2

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