Water → ethyl (4-[3-tert-butyl-5-[(phenoxycarbonyl)amino]-1H-pyrazol-1-yl]phenyl)acetate

HRID 1174850노트

반응식

HRID 1174850 반응식
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:16]([NH2:17])=[CH:15][C:14]([C:18]([CH3:21])([CH3:20])[CH3:19])=[N:13]2)=[CH:8][CH:7]=1)[CH3:2].C([O-])([O-])=O.[K+].[K+].Cl[C:30]([O:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:31].O>C1COCC1.CCOC(C)=O>[CH2:1]([O:3][C:4](=[O:22])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:16]([NH:17][C:30]([O:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[O:31])=[CH:15][C:14]([C:18]([CH3:21])([CH3:20])[CH3:19])=[N:13]2)=[CH:8][CH:7]=1)[CH3:2]

참가 물질

7

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 15891Phenyl chloroformateHCID 59557934ethyl [4-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)phenyl]acetate

생성물 1

HCID 59557923ethyl (4-[3-tert-butyl-5-[(phenoxycarbonyl)amino]-1H-pyrazol-1-yl]phenyl)acetate수율 76%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a suspension of ethyl[4-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)phenyl]acetate (10 g, 33.2 mmol) and K2CO3 (9.17 g, 66.4 mmol) in THF (300 mL) was added phenyl chloroformate (8.61 mL, 66.4 mmol), and the resulting reaction mixture was stirred at room temperature overnight. The mixture was poured into a mixture of water and EtOAc and the organic phase was separated and dried over Na2SO4, concentrated at reduced pressure to afford a brown syrup, which was purified by MPLC (0% to 20% EtOAc in hexane). The desired product was obtained as a white solid (10.6 g) in 76% yield. 1H-NMR (CD2Cl2-d2) δ 7.51-7.10 (m, 10H), 6.47 (s, 1H), 4.16 (q, J=7.1 Hz, 2H), 3.71 (s, 2H), 1.37 (s, 9H), 1.28 (t, J=7.0 Hz, 3H).

후처리

  1. customthe resulting reaction mixture
  2. customthe organic phase was separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated at reduced pressure
  5. customto afford a brown syrup, which
  6. customwas purified by MPLC (0% to 20% EtOAc in hexane)

출처 및 근거

ORD 기록
ord-d87063d7013a41608eb4cfc9488bf05b
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07838524B2

반응 노트

불러오는 중…