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

HRID 18442

Reaktionsgleichung

Reaktionsgleichung von HRID 18442
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]

Komponenten

4

Edukt 2

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

Produkt 1

HCID 99718412-Hydroxy-4-[4-(3-hydroxy-prop-1-ynyl)-benzylamino]-benzoic acidAusbeute 17,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21881883Oxolane--water (1/1)Lösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

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.

Aufarbeitung

  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%)

Quellen und Nachweise

ORD-Eintrag
ord-f0f357f9ec75423a8a0a3472c5a90508
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741352B2

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