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Metaperiodic acid → 3-(2-{[4-Chloro-3-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-benzoyl]-methyl-amino}-phenoxy)-2,2-dimethyl-propionic acid

HRID 1486024
ノート
印刷プレビュー

反応式

HRID 1486024 の反応式
I(O)(=O)(=O)=[O:2].[Cl:6][C:7]1[CH:29]=[CH:28][C:10]([C:11]([N:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21][CH2:22][C:23]([CH3:27])([CH3:26])[CH2:24][OH:25])[CH3:14])=[O:12])=[CH:9][C:8]=1[C:30]1[CH:31]=[N:32][C:33]([C:38]([F:41])([F:40])[F:39])=[CH:34][C:35]=1[C:36]#[N:37]>CC#N>[Cl:6][C:7]1[CH:29]=[CH:28][C:10]([C:11]([N:13]([CH3:14])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21][CH2:22][C:23]([CH3:27])([CH3:26])[C:24]([OH:2])=[O:25])=[O:12])=[CH:9][C:8]=1[C:30]1[CH:31]=[N:32][C:33]([C:38]([F:41])([F:39])[F:40])=[CH:34][C:35]=1[C:36]#[N:37]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 65185Metaperiodic acidHCID 686025284-chloro-3-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-N-[2-(3-hydroxy-2,2-dimethyl-propoxy)-phenyl]-N-methyl-benzamide

生成物 1

HCID 593703443-(2-{[4-Chloro-3-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-benzoyl]-methyl-amino}-phenoxy)-2,2-dimethyl-propionic acid

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒2 回

反応条件

温度
0 °C

実験手順

To periodic acid (68 mg, 0.30 mmol) in CH3CN (200 μL) at 0° C., Cr(VI)oxide (0.7 mg, 0.0073 mmol) was added and the mixture was stirred for 15 min at 0° C. A solution of 4-chloro-3-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-N-[2-(3-hydroxy-2,2-dimethyl-propoxy)-phenyl]-N-methyl-benzamide (29 mg, 0.056 mmol) dissolved in CH3CN (200 μL) was added and the mixture was warmed to rt. After 2 hr at rt, the mixture was filtered, rinsed with CH3CN, concentrated, dissolved in MeOH and purified by prep HPLC yielding 3-(2-{[4-chloro-3-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-benzoyl]-methyl-amino}-phenoxy)-2,2-dimethyl-propionic acid 52-1. MS: 532.3 (M+H)+, tR=3.65 min (method 3).

後処理

  1. additionwas added
  2. temperaturethe mixture was warmed to rt
  3. waitAfter 2 hr at rt
  4. filtrationthe mixture was filtered
  5. washrinsed with CH3CN
  6. concentrationconcentrated
  7. dissolutiondissolved in MeOH
  8. custompurified by prep HPLC

出典と根拠

ORDレコード
ord-ed0bc31022de4bfc8701d06a35414a16
出典データセット
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09422310B2

反応ノート

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