Sodium Hydroxide → [5-tert-Butyl-2-(3-methyl-5-triisopropylsilanyloxy-phenyl)-2H-pyrazol-3-yl]-carbamic acid 2,2,2-trichloro-ethyl ester

HRID 711165ノート

反応式

HRID 711165 の反応式
[C:1]([C:5]1[CH:6]=[C:7]([NH2:28])[N:8]([C:10]2[CH:15]=[C:14]([O:16][Si:17]([CH:24]([CH3:26])[CH3:25])([CH:21]([CH3:23])[CH3:22])[CH:18]([CH3:20])[CH3:19])[CH:13]=[C:12]([CH3:27])[CH:11]=2)[N:9]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl[C:32]([O:34][CH2:35][C:36]([Cl:39])([Cl:38])[Cl:37])=[O:33]>C(OCC)(=O)C>[Cl:37][C:36]([Cl:39])([Cl:38])[CH2:35][O:34][C:32](=[O:33])[NH:28][C:7]1[N:8]([C:10]2[CH:15]=[C:14]([O:16][Si:17]([CH:18]([CH3:20])[CH3:19])([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:22])[CH3:23])[CH:13]=[C:12]([CH3:27])[CH:11]=2)[N:9]=[C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[CH:6]=1

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 870632,2,2-Trichloroethyl chloroformateHCID 1233019165-tert-Butyl-2-(3-methyl-5-triisopropylsilanyloxy-phenyl)-2H-pyrazol-3-ylamine

生成物 1

HCID 123538151[5-tert-Butyl-2-(3-methyl-5-triisopropylsilanyloxy-phenyl)-2H-pyrazol-3-yl]-carbamic acid 2,2,2-trichloro-ethyl ester収率 103%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒2 回

実験手順

To a solution of Intermediate 54b (0.73 g, assumed 1.70 mmol) in ethyl acetate (8 mL) was added 1N sodium hydroxide solution (4.5 mL, 4.50 mmol). Stirred for 5 min then 2,2,2-trichloroethyl chloroformate (275 μL, 2.00 mmol) was added and the mixture stirred vigorously at RT for 3.5 h. Diluted with EtOAc, washed with water and brine, dried, and concentrated in vacuo. The residue was purified by FCC, using 0-15% EtOAc in cyclohexane, to give the still impure title compound (1.01 g). NMR (300 MHz, CDCl3): inter alia 1.02-1.15 (18H, m), 1.18-1.38 (12H, m), 2.34 (3H, s), 4.82 (2H, s), 6.43 (1H, s), 6.69-6.77 (2H, m), 6.84-6.96 (2H, m).

後処理

  1. stirringthe mixture stirred vigorously at RT for 3.5 h
  2. washwashed with water and brine
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by FCC

出典と根拠

ORDレコード
ord-a48b32d69f1f4f4da80c6b2152b65769
出典データセット
uspto-grants-2015_11
特許番号
US09181242B2

反応ノート

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