Sodium Hydroxide → 5-[(2R)-2-({(2R)-2-{[tert-butyl(dimethyl)silyl]oxy}-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl}amino)propyl]-1H-indole-2-carboxylic acid

HRID 1760714ノート

反応式

HRID 1760714 の反応式
[Si:1]([O:8][C@H:9]([C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[C:30]([CH2:35][OH:36])[CH:29]=1)[CH2:10][NH:11][C@H:12]([CH3:27])[CH2:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[NH:19][C:18]([C:23]([O:25]C)=[O:24])=[CH:17]2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[OH-].[Na+]>O1CCOCC1.O>[Si:1]([O:8][C@H:9]([C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[C:30]([CH2:35][OH:36])[CH:29]=1)[CH2:10][NH:11][C@H:12]([CH3:27])[CH2:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[NH:19][C:18]([C:23]([OH:25])=[O:24])=[CH:17]2)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 12988831methyl 5-[(2R)-2-({(2R)-2-{[tert-butyl(dimethyl)silyl]oxy}-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl}amino)propyl]-1H-indole-2-carboxylate

生成物 1

HCID 129888305-[(2R)-2-({(2R)-2-{[tert-butyl(dimethyl)silyl]oxy}-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl}amino)propyl]-1H-indole-2-carboxylic acid

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

A solution of methyl 5-[(2R)-2-({(2R)-2-{[tert-butyl(dimethyl)silyl]oxy}-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl}amino)propyl]-1H-indole-2-carboxylate (Preparation 12, 0.30 g, 0.59 mmol) in 1,4-dioxane (10 ml) was treated with a solution of sodium hydroxide (59 mg, 1.46 mmol) in water (1 ml) and the resulting mixture left to stir at room temperature for 30 minutes. After this time the reaction mixture was heated to 90° C. for 30 minutes and then cooled to room temperature. The solvent was removed in vacuo and the residue re-dissolved in water (20 ml) and pH adjusted to 7 by addition of 2N Hydrochloric acid. The solid that formed was filtered off, solubilised in a mixture of dichloromethane and methanol (20 ml 90:10 by volume), dried (magnesium sulphate) and the solvent removed in vacuo to give the title compound as a pale orange foam.

後処理

  1. waitthe resulting mixture left
  2. temperatureAfter this time the reaction mixture was heated to 90° C. for 30 minutes
  3. temperaturecooled to room temperature
  4. customThe solvent was removed in vacuo
  5. dissolutionthe residue re-dissolved in water (20 ml)
  6. additionpH adjusted to 7 by addition of 2N Hydrochloric acid
  7. customThe solid that formed
  8. filtrationwas filtered off
  9. additionsolubilised in a mixture of dichloromethane and methanol (20 ml 90:10 by volume)
  10. dry with materialdried (magnesium sulphate)
  11. customthe solvent removed in vacuo

出典と根拠

ORDレコード
ord-07ce2805679a4f9d9c3302097081481b
出典データセット
uspto-grants-2005_01
特許番号
US06844362B2

反応ノート

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