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1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → isopropyl 2-(3-(6-Hexyl-1-naphthamido)phenoxy)acetate

HRID 472783
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 472783
Cl.C(N=C=NCCCN(C)C)C.[CH2:13]([C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[C:25]([C:29]([OH:31])=O)=[CH:24][CH:23]=[CH:22]2)[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[NH2:32][C:33]1[CH:34]=[C:35]([CH:44]=[CH:45][CH:46]=1)[O:36][CH2:37][C:38]([O:40][CH:41]([CH3:43])[CH3:42])=[O:39]>C(Cl)Cl>[CH2:13]([C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[C:25]([C:29]([NH:32][C:33]1[CH:34]=[C:35]([CH:44]=[CH:45][CH:46]=1)[O:36][CH2:37][C:38]([O:40][CH:41]([CH3:42])[CH3:43])=[O:39])=[O:31])=[CH:24][CH:23]=[CH:22]2)[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10608474Isopropyl 2-(3-aminophenoxy)acetateHCID 543973816-Hexyl-1-naphthoic acid

Produkt 1

HCID 66660445isopropyl 2-(3-(6-Hexyl-1-naphthamido)phenoxy)acetateAusbeute 23,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

1-Ethyl-3-(3′-dimethylaminopropyl)-carbodiimide hydrochloride (EDCI, 157 mg) was added to a solution of 6-hexyl-1-naphthoic acid (161 mg, 0.63 mmol) and isopropyl 2-(3-aminophenoxy)acetate (131 mg, 0.63 mmol) in CH2Cl2 (6.3 mL) and the solution was stirred at room temperature overnight. The reaction was concentrated in vacuo, diluted with water (25 mL) and extracted with EtOAc (2×25 mL). The combined organic phase was washed with 1 N aqueous HCl (20 mL), saturated aqueous NaHCO3 (20 mL) and brine (20 mL), then dried (Na2SO4), filtered and concentrated in vacuo. The crude residue was purified on 40 g silica (100% hexanes→100% EtOAc, gradient) to afford 65 mg (23%) of isopropyl 2-(3-(6-Hexyl-1-naphthamido)phenoxy)acetate.

Aufarbeitung

  1. concentrationThe reaction was concentrated in vacuo
  2. additiondiluted with water (25 mL)
  3. extractionextracted with EtOAc (2×25 mL)
  4. washThe combined organic phase was washed with 1 N aqueous HCl (20 mL), saturated aqueous NaHCO3 (20 mL) and brine (20 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude residue was purified on 40 g silica (100% hexanes→100% EtOAc, gradient)

Quellen und Nachweise

ORD-Eintrag
ord-04577eb0cbab4094956826a2102e533e
Quelldatensatz
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08633220B2

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