Sodium Hydroxide → HCID 22010336、化合物

HRID 322895

反応式

HRID 322895 の反応式
[C:1]([C:9]1[CH:32]=[CH:31][C:30]([O:33][CH2:34][C:35]2[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=2)=[CH:29][C:10]=1[O:11][CH:12]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[CH3:28])[CH2:13][CH2:14][C:15]([O:17]C(C)(C)C)=[O:16])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO.O1CCCC1>[C:1]([C:9]1[CH:32]=[CH:31][C:30]([O:33][CH2:34][C:35]2[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=2)=[CH:29][C:10]=1[O:11][CH:12]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[CH3:28])[CH2:13][CH2:14][C:15]([OH:17])=[O:16])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 22010469Tert-butyl 4-[2-benzoyl-5-(pyridin-3-ylmethoxy)phenoxy]-4-(2-methylphenyl)butanoate

生成物 1

HCID 22010336HCID 22010336、化合物

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of tert-butyl 4-[2-benzoyl-5-(pyridin-3-ylmethoxy)phenoxy]-4-(2-methylphenyl)butanoate, thought to be the (R)-enantiomer, (1 g) in a mixture of methanol (10 mL) and tetrahydrofuran (10 mL) is treated with 5 M aqueous sodium hydroxide solution (7.5 mL) and the reaction stirred at ambient temperature for 24 hours. The reaction is concentrated to low volume, acidified to pH 5 with dilute hydrochloric acid, and extracted into dichloromethane (2×30 mL). The combined organic layers are washed with brine, dried over magnesium sulphate, filtered and concentrated under reduced pressure to leave a yellow gum. Trituration with diethyl ether and recrystallization of the resultant solid from acetonitrile containing a little decolourizing charcoal gives 4-[2-benzoyl-5-(pyridin-3-ylmethoxy)phenoxy]-4-(2-methylphenyl)butanoic acid, thought to be the (R)-enantiomer, (0.2 g) as a pale yellow solid, m.p. 185-186° C. [Elemental analysis:- C, 74.83; H, 5.65; N, 2.91%; Calculated:- C, 75.01; H, 5.72; N,2.87%].

後処理

  1. concentrationThe reaction is concentrated to low volume
  2. extractionextracted into dichloromethane (2×30 mL)
  3. washThe combined organic layers are washed with brine
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto leave a yellow gum
  8. customTrituration with diethyl ether and recrystallization of the resultant solid from acetonitrile containing a little decolourizing charcoal

出典と根拠

ORDレコード
ord-bfb5ab2d05994a88bdb79b7325fd9e7d
出典データセット
uspto-grants-2001_04
特許番号
US06211234B1

関連ノート

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