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

HRID 1944127Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1944127
[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-08da8659f6064b99b414e5bf160354f0
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08394826B2

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