Phthalic Anhydride → (2S)-5-(Benzyloxy)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-5-oxopentanoic acid

HRID 622792

Reaktionsgleichung

Reaktionsgleichung von HRID 622792
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9]([CH2:11][CH2:12][C@H:13]([NH2:17])[C:14]([OH:16])=[O:15])=[O:10])=[CH:3][CH:2]=1.[C:18]1(=O)[O:23][C:21](=[O:22])[C:20]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:19]12>C1(C)C=CC=CC=1>[CH2:7]([O:8][C:9]([CH2:11][CH2:12][C@H:13]([N:17]1[C:21](=[O:22])[C:20]2[C:19](=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:18]1=[O:23])[C:14]([OH:16])=[O:15])=[O:10])[C:4]1[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1

Komponenten

4

Edukt 2

HCID 6811Phthalic AnhydrideHCID 122337L-Glutamic acid, 5-(phenylmethyl) ester

Produkt 1

HCID 11100670(2S)-5-(Benzyloxy)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-5-oxopentanoic acidAusbeute 60,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

16 g of L-glutamic acid γ-benzyl ester and 11 g of phthalic anhydride, both finely powdered, were stirred in 20 ml of toluene at reflux temperature for 2 hours. 50 ml of toluene were added and the mixture was evaporated. A further 80 ml of toluene were then added and the mixture was left to crystallize. Recrystallization from toluene yielded 15 g of α(S)-(2-benzyloxycarbonylethyl)-1,3-dihydro-1,3-dioxo-2-isoindoleacetic acid of melting point 96°-98° C.; [α]D20 =-50.4° (c=1 in methanol).

Aufarbeitung

  1. temperatureat reflux temperature for 2 hours
  2. customthe mixture was evaporated
  3. additionA further 80 ml of toluene were then added
  4. waitthe mixture was left
  5. customto crystallize
  6. customRecrystallization from toluene

Quellen und Nachweise

ORD-Eintrag
ord-53de2e23dd3245e084f4c8875811a97d
Quelldatensatz
uspto-grants-1988_09
Patentnummer
US04772701

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