Hydrochloric Acid → HCID 178474531、化合物

HRID 554647ノート

反応式

HRID 554647 の反応式
C1CCCCC=1.O1CCCC1.B.[CH2:13]([N:20]([CH2:24][C:25]1[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:27][C:26]=1[C:35]1[C:36]([O:43]C)=[N:37][CH:38]=[C:39]([C:41]#[CH:42])[CH:40]=1)[C:21](=[O:23])[CH3:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[OH-:45].[Na+].[OH:47]O.Cl>C1COCC1.CO>[C:21]([N:20]([CH2:24][C:25]1[CH:30]=[C:29]([C:31]([F:32])([F:33])[F:34])[CH:28]=[CH:27][C:26]=1[C:35]1[CH:40]=[C:39]([CH2:41][C:42]([OH:47])=[O:45])[CH:38]=[N:37][C:36]=1[OH:43])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:23])[CH3:22]

参加物

9

反応物 6

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 8079CyclohexeneHCID 14798Sodium HydroxideHCID 2723981Borane;tetrahydrofuranHCID 86640542N-Benzyl-N-[2-(5-ethynyl-2-methoxy-pyridin-3-yl)-5-trifluoromethyl-benzyl]-acetamide

生成物 1

HCID 178474531HCID 178474531、化合物

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To cyclohexene (0.20 mL, 1.98 mmol) at room temperature was added borane tetrahydrofuran complex (1M in THF; 1.01 mL, 1.01 mmol), and the reaction was stirred for 45 minutes. N-Benzyl-N-[2-(5-ethynyl-2-methoxy-pyridin-3-yl)-5-trifluoromethyl-benzyl]-acetamide (0.126 g, 0.29 mmol) in THF (2 mL) was added dropwise, and the reaction was stirred for 2 hours at room temperature. The mixture was cooled to 0° C., and MeOH (1 mL) and 1N aqueous NaOH (1.01 mL, 1.01 mmol) were added, followed by hydrogen peroxide (30%; 0.31 mL, 3.00 mmol), and the reaction was stirred for 1 hour at 0° C. The mixture was acidified with 1N aqueous HCl and extracted with EtOAc, and the combined organic layers were dried, filtered, and concentrated. The residue was purified by preparative HPLC to give (5-{2-[(N-Acetyl-N-benzyl-amino)-methyl]-4-trifluoromethyl-phenyl}-6-hydroxy-pyridin-3-yl)-acetic acid.

後処理

  1. stirringthe reaction was stirred for 2 hours at room temperature
  2. stirringthe reaction was stirred for 1 hour at 0° C
  3. extractionextracted with EtOAc
  4. customthe combined organic layers were dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by preparative HPLC

出典と根拠

ORDレコード
ord-b64b1b78bde446c1a970ae2f4fd9107a
出典データセット
uspto-grants-2011_11
特許番号
US08049015B2

反応ノート

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