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

HRID 221879ノート

反応式

HRID 221879 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-072dba7c4d1b4f5a8d09e940966cd4da
出典データセット
uspto-grants-2012_06
特許番号
US08207166B2

反応ノート

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