Lithium hydroxide, monohydrate → 2-(2-Carboxy-2-(4-(triisopropylsilyloxy)phenyl)ethylcarbamoyl)benzoic acid

HRID 1020087Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1020087
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH:13]([C:18]1[CH:23]=[CH:22][C:21]([O:24][Si:25]([CH:32]([CH3:34])[CH3:33])([CH:29]([CH3:31])[CH3:30])[CH:26]([CH3:28])[CH3:27])=[CH:20][CH:19]=1)[C:14]([O:16]C)=[O:15].[OH:35][Li].O>C1COCC1.O>[C:14]([CH:13]([C:18]1[CH:23]=[CH:22][C:21]([O:24][Si:25]([CH:29]([CH3:30])[CH3:31])([CH:32]([CH3:33])[CH3:34])[CH:26]([CH3:27])[CH3:28])=[CH:20][CH:19]=1)[CH2:12][NH:3][C:2]([C:10]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:4]([OH:35])=[O:11])=[O:1])([OH:16])=[O:15]

Komponenten

4

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 59563757Methyl 3-(1,3-dioxoisoindolin-2-yl)-2-(4-(triisopropylsilyloxy)phenyl)propanoate

Produkt 1

HCID 595637882-(2-Carboxy-2-(4-(triisopropylsilyloxy)phenyl)ethylcarbamoyl)benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

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

Versuchsvorschrift

To methyl 3-(1,3-dioxoisoindolin-2-yl)-2-(4-(triisopropylsilyloxy)phenyl)propanoate (E3) in THF/H2O was added LiOH.H2O, and the solution was stirred for 1.5 h or until conversion to product was visible by LC-MS. The solution was then poured into EtOAc/NH4Cl(sat)/1 N HCl (3:1), and the aqueous layer was further extracted with EtOAc. The organics were dried (Na2SO4), filtered, evaporated, and dried to give crude 2-(2-carboxy-2-(4-(triisopropylsilyloxy)phenyl)ethylcarbamoyl)benzoic acid (E4).

Aufarbeitung

  1. extractionthe aqueous layer was further extracted with EtOAc
  2. dry with materialThe organics were dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-caa8bd69ffb84c28863b963f6bb9bdf4
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08716310B2

Notizen zur Reaktion

Wird geladen…