Lithium Hydroxide → 2-Hydroxy-4-[4-(3-hydroxy-prop-1-ynyl)-benzylamino]-benzoic acid

HRID 18442

反応式

HRID 18442 の反応式
C[O:2][C:3](=[O:23])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]#[C:19][CH2:20][OH:21])=[CH:14][CH:13]=2)=[CH:6][C:5]=1[OH:22].[Li+].[OH-]>C1COCC1.O>[OH:22][C:5]1[CH:6]=[C:7]([NH:10][CH2:11][C:12]2[CH:13]=[CH:14][C:15]([C:18]#[C:19][CH2:20][OH:21])=[CH:16][CH:17]=2)[CH:8]=[CH:9][C:4]=1[C:3]([OH:23])=[O:2]

参加物

4

反応物 2

HCID 3939Lithium HydroxideHCID 586858312-Hydroxy-4-[4-(3-hydroxy-prop-1-ynyl)-benzylamino]-benzoic acid methyl ester

生成物 1

HCID 99718412-Hydroxy-4-[4-(3-hydroxy-prop-1-ynyl)-benzylamino]-benzoic acid収率 17.3%

試薬・触媒・溶媒 1

HCID 21881883Oxolane--water (1/1)溶媒

反応条件

温度
90 °C

実験手順

2-Hydroxy-4-[4-(3-hydroxy-prop-1-ynyl)-benzylamino]-benzoic acid methyl ester (22 mg; 0.07 mmol) was dissolved in THF/H2O (1 mL/0.25 mL) and LiOH was added (17 mg; 0.7 mmol). The reaction mixture was heated to 90° C. for 1 hour. THF was removed by evaporation and EtOAc (3 mL) and H2O (0.5 mL) was added. The organic phase was isolated, dried (Na2SO4), filtered, evaporated to dryness and purified by flash column chromatography (SiO2-PE80-100° C./EtOAc/CH3COOH=1:1:1%) to yield 3.6 mg (17%) of pure product.

後処理

  1. customTHF was removed by evaporation and EtOAc (3 mL) and H2O (0.5 mL)
  2. additionwas added
  3. customThe organic phase was isolated
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated to dryness
  7. custompurified by flash column chromatography (SiO2-PE80-100° C./EtOAc/CH3COOH=1:1:1%)

出典と根拠

ORDレコード
ord-f0f357f9ec75423a8a0a3472c5a90508
出典データセット
uspto-grants-2010_06
特許番号
US07741352B2

関連ノート

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