Ammonium Chloride → N-[3-(4-tert-butylcyclohexan-1-yl)phenyl]-4-(2-hydroxyethyloxy)-3-methoxyphenylacetamide

HRID 7081

Reaktionsgleichung

Reaktionsgleichung von HRID 7081
[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:12]=[C:13]([NH:17][C:18](=[O:35])[CH2:19][C:20]3[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28](OCC)=[O:29])=[C:22]([O:33][CH3:34])[CH:21]=3)[CH:14]=[CH:15][CH:16]=2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].C(C1CCC(C2C=C(NC(=O)C(OC)C3C=CC(C(O)=O)=C(OC)C=3)C=CC=2)CC1)(C)(C)C.[BH4-].[Na+].[Cl-].[NH4+]>C(O)C>[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:12]=[C:13]([NH:17][C:18](=[O:35])[CH2:19][C:20]3[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][OH:29])=[C:22]([O:33][CH3:34])[CH:21]=3)[CH:14]=[CH:15][CH:16]=2)[CH2:7][CH2:6]1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 4

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 22019614n-[3-(4-Tert-butylcyclohexan-1-yl)phenyl]-4-carboxy-methyloxy-3-methoxyphenylacetamideHCID 22019615N-[3-(4-tert-Butylcyclohexan-1-yl)phenyl]-4-ethoxycarbonylmethyloxy-3-methoxyphenylacetamide

Produkt 1

HCID 22019643N-[3-(4-tert-butylcyclohexan-1-yl)phenyl]-4-(2-hydroxyethyloxy)-3-methoxyphenylacetamideAusbeute 50,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

N-[3-(4-tert-Butylcyclohexan-1-yl)phenyl]-4-ethoxycarbonylmethyloxy-3-methoxyphenylacetamide (240 mg), which is an intermediate of Example 72, is dissolved in ethanol, and thereto is added sodium borohydride (35 mg), and the mixture is stirred at room temperature for 2 hours. A saturated aqueous ammonium chloride solution is added thereto, and the mixture is extracted with chloroform. The extracted is washed with water, and the solvent is evaporated under reduced pressure. The residue is purified by silica gel column chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate) to give the desired compound (110 mg).

Aufarbeitung

  1. extractionthe mixture is extracted with chloroform
  2. washThe extracted is washed with water
  3. customthe solvent is evaporated under reduced pressure
  4. customThe residue is purified by silica gel column chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-3bac02c0740548d09986b5f0c85dc5c5
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07084176B2

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