Water → 4-[(15-Tert-butoxycarbonylpentadecanoylamino)methyl]benzoic acid

HRID 562543Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 562543
[NH2:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.O=C1CCC(=O)N1[O:19][C:20](=O)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36].O>CN1C(=O)CCC1>[C:38]([O:37][C:35]([CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][C:20]([NH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([OH:9])=[O:8])=[CH:10][CH:11]=1)=[O:19])=[O:36])([CH3:41])([CH3:40])[CH3:39]

Komponenten

5

Edukt 3

HCID 962WaterHCID 655264-(Aminomethyl)Benzoic AcidHCID 595628071-tert-Butyl 16-(2,5-dioxopyrrolidin-1-yl) hexadecanedioate

Produkt 1

HCID 596879104-[(15-Tert-butoxycarbonylpentadecanoylamino)methyl]benzoic acidAusbeute 65,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

To 4-(Aminomethyl)benzoic acid (0.2 g, 1.32 mmol) was added in NMP (5 mL). Hexadecanedioic acid tert-butyl ester 2,5-dioxo-pyrrolidin-1-yl ester (0.58 g, 1.32 mmol) was added and the mixture was stirred at room temperature overnight. The mixture was poured into water (100 mL), the precipitate was isolated by filtration and dried in vacuo. The crude material was recrystallized from toluene to give 4-[(15-tert-butoxycarbonylpentadecanoylamino)methyl]benzoic acid (413 mg).

Aufarbeitung

  1. customthe precipitate was isolated by filtration
  2. customdried in vacuo
  3. customThe crude material was recrystallized from toluene

Quellen und Nachweise

ORD-Eintrag
ord-d3a1e6cf16e84016b65969a10e52caed
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08067362B2

Notizen zur Reaktion

Wird geladen…