Tetrabutylammonium Fluoride → 2-{2-[2-Carboxy-2-(1,3-dioxo-1,3,dihydro-isoindol-2-yl)-ethyl]-benzylamino}-4-methyl-valeric acid, tert-butyl ester

HRID 2715

Reaktionsgleichung

Reaktionsgleichung von HRID 2715
[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[CH:12]([C:34]([O:36]CC[Si](C)(C)C)=[O:35])[CH2:13][C:14]1[CH:33]=[CH:32][CH:31]=[CH:30][C:15]=1[CH2:16][NH:17][CH:18]([CH2:26][CH:27]([CH3:29])[CH3:28])[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:34]([CH:12]([N:3]1[C:4](=[O:11])[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2]1=[O:1])[CH2:13][C:14]1[CH:33]=[CH:32][CH:31]=[CH:30][C:15]=1[CH2:16][NH:17][CH:18]([CH2:26][CH:27]([CH3:29])[CH3:28])[C:19]([O:21][C:22]([CH3:24])([CH3:23])[CH3:25])=[O:20])([OH:36])=[O:35]

Komponenten

4

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 1317205832-{2-[2-(1,3-Dioxo-1,3,dihydro-isoindol-2-yl)-2-(2-trimethylsilanyl-ethoxycarbonyl)-ethyl]-benzylamino}-4-methyl-valeric acid, tert-butyl ester

Produkt 1

HCID 1317205842-{2-[2-Carboxy-2-(1,3-dioxo-1,3,dihydro-isoindol-2-yl)-ethyl]-benzylamino}-4-methyl-valeric acid, tert-butyl esterAusbeute 102,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Dissolve 2-{2-[2-(1,3-dioxo-1,3,dihydro-isoindol-2-yl)-2-(2-trimethylsilanyl-ethoxycarbonyl)-ethyl]-benzylamino}-4-methyl-valeric acid, tert-butyl ester (221 mg, 0.372 mmol) in tetrahydrofuran (5 mL) and treat with tetrabutylammonium fluoride (0.43 mL of a 1.0M solution in tetrahydrofuran, 0.43 mmol). Stir for 1.5 hours, evaporate the solvent in vacuo and dissolve the residue in ethyl acetate (75 mL). Wash with 1N hydrochloric acid (25 mL) and brine (25 mL). Dry (Na2SO4) and evaporate the solvent in vacuo to give the title compound as a white solid (188 mg).

Aufarbeitung

  1. customevaporate the solvent in vacuo
  2. dissolutiondissolve the residue in ethyl acetate (75 mL)
  3. washWash with 1N hydrochloric acid (25 mL) and brine (25 mL)
  4. dry with materialDry (Na2SO4)
  5. customevaporate the solvent in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6b6484c542a4422eb9a68c56a12b0a18
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05731306

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