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

HRID 445003Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 445003
[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 recrystalized 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 recrystalized from toluene

Quellen und Nachweise

ORD-Eintrag
ord-5ab31b71d78142d5b466c4c7cace2c19
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476228B2

Notizen zur Reaktion

Wird geladen…