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

HRID 18442

반응식

HRID 18442 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 21881883Oxolane--water (1/1)용매

반응 조건

온도
90 °C

실험 절차

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.

후처리

  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%)

출처 및 근거

ORD 기록
ord-f0f357f9ec75423a8a0a3472c5a90508
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741352B2

연결된 노트

불러오는 중…