Hydrochloric Acid → 3-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-4-methoxybenzoic acid

HRID 1976772Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1976772
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([OH:7])=[O:6].[C:13](C1CC(=O)NC1=O)([O:15][CH2:16][CH:17]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]2[C:18]1=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:14].Cl>CC(C)=O.C([O-])(O)=O.[Na+]>[CH:28]1[C:29]2[CH:17]([CH2:16][O:15][C:13]([NH:1][C:2]3[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=3[O:11][CH3:12])[C:5]([OH:7])=[O:6])=[O:14])[C:18]3[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:24]=2[CH:25]=[CH:26][CH:27]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 178233-Amino-4-methoxybenzoic acidHCID 9883579Fmoc-succinimide

Produkt 1

HCID 109161113-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-4-methoxybenzoic acidAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittel2×HCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

A suspension of 3-amino-4-methoxybenzoic acid (1.00 g, 6.0 mmol) in acetone (15 mL) was treated portionwise and alternately with Fmoc-succinimide (2.63 g, 7.8 mmol) in acetone (15 mL) and saturated aqueous NaHCO3 to keep the pH of the solution between 8-9, stirred at room temperature for 18 hours, treated with 3M HCl, and filtered. The solid was washed sequentially with water and dichloromethane and dried under vacuum to provide 1.54 g (66%) of the desired product.

Aufarbeitung

  1. filtrationfiltered
  2. washThe solid was washed sequentially with water and dichloromethane
  3. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-77271e2aa0054f4ea958b17ed33b6da9
Quelldatensatz
uspto-grants-2001_05
Patentnummer
US06228868B1

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