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Ammonia → HCID 67717719, Verbindung

HRID 1683820
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1683820
[ClH:1].[CH2:2]([O:4][C:5]([CH2:7][O:8][C:9]1[CH:10]=[C:11]([CH:30]=[CH:31][C:32]=1[C:33]([N:35]([CH:39]([CH3:41])[CH3:40])[CH:36]([CH3:38])[CH3:37])=[O:34])[O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25](=[NH:29])OCC)=[CH:21][CH:20]=1)=[O:6])[CH3:3].[OH-].[Na+].[Cl-].[NH4+].N.Cl.[NH2:48]N=CC1C=CC(OCCCCCOC2C=CC(C(=O)N(C(C)C)C(C)C)=C(C=2)OCC(O)=O)=CC=1.Cl>C(O)C>[ClH:1].[NH2:48][N:29]=[CH:25][C:22]1[CH:23]=[CH:24][C:19]([O:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][O:12][C:11]2[CH:30]=[CH:31][C:32]([C:33](=[O:34])[N:35]([CH:39]([CH3:41])[CH3:40])[CH:36]([CH3:38])[CH3:37])=[C:9]([CH:10]=2)[O:8][CH2:7][C:5]([O:4][CH2:2][CH3:3])=[O:6])=[CH:20][CH:21]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 6

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 19040952HCID 19040952, VerbindungHCID 67634873HCID 67634873, Verbindung

Produkt 1

HCID 67717719
HCID 67717719, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A stirred, 0° C. solution of ethyl 4-[5-[3-ethoxycarbonylmethoxy-4-[N,N-bis(1-methylethyl)aminocarbonyl]phenoxy]pentyloxy]benzenecarboximidoate monohydrochloride (400 mg, 0.68 mmol) in 25 mL of anhydrous ethanol is treated with 1.36 mL of 1.0N aqueous sodium hydroxide. After stirring 1.5 hours, the reaction is concentrated in vacuo. The resulting 5-[5-[4-(ethoxyiminomethyl)phenoxy]pentyloxy]-2-[N,N-bis(1-methylethyl)carbamoyl]phenoxyacetic acid is then dissolved in 50 mL of anhydrous ethanol in a pressure tube, and treated with ammonium chloride (500 mg, 9.4 mmol). This mixture is treated with anhydrous ammonia for 2 minutes at 0° C. The pressure tube is sealed and heated to 50° C. for 1 hour. Upon cooling and concentrating in vacuo, the resulting material is purified by chromatography on silica gel (15 g) with 20-30% methanol/dichloromethane as the eluent to afford a colorless foam. The resulting 5-[5-[4-(aminoiminomethyl)phenoxy]pentyloxy]-2-[N,N-bis(1-methylethyl)carbamoyl]phenoxyacetic acid monohydrochloride is then dissolved in 150 mL of anhydrous ethanol at 0° C. and treated with anhydrous hydrogen chloride gas over 30 minutes. This solution is stirred at room temperature for 20 hours and the resulting solution is concentrated in vacuo. The resulting material is purified by chromatography on silica gel (15 g) with 5-20% methanol/dichloromethane as the eluent to afford ethyl 5-[5-[4-(aminoiminomethyl)phenoxy]pentyloxy]-2-[N,N-bis(1-methylethyl)carbamoyl]phenoxyacetate monohydrochloride as colorless foam; CHN calculated for

Aufarbeitung

  1. concentrationthe reaction is concentrated in vacuo
  2. dissolutionThe resulting 5-[5-[4-(ethoxyiminomethyl)phenoxy]pentyloxy]-2-[N,N-bis(1-methylethyl)carbamoyl]phenoxyacetic acid is then dissolved in 50 mL of anhydrous ethanol in a pressure tube
  3. customThe pressure tube is sealed
  4. temperatureUpon cooling
  5. concentrationconcentrating in vacuo
  6. customthe resulting material is purified by chromatography on silica gel (15 g) with 20-30% methanol/dichloromethane as the eluent
  7. customto afford a colorless foam
  8. stirringThis solution is stirred at room temperature for 20 hours
  9. concentrationthe resulting solution is concentrated in vacuo
  10. customThe resulting material is purified by chromatography on silica gel (15 g) with 5-20% methanol/dichloromethane as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-64656c1986774fb5a93dfe5dd8bb252b
Quelldatensatz
uspto-grants-1997_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05639768

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