1,1-Dichloroethane → 3-Cyclohexyl-N-(3,3-dimethyl-butyl)-3-[(5-nitro-2-phenoxy-pyridin-4-ylmethyl)-amino]-propionamide

HRID 491912Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 491912
[NH2:1][CH:2]([CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[CH2:3][C:4]([NH:6][CH2:7][CH2:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:5].[N+:19]([C:22]1[C:23]([CH:35]=O)=[CH:24][C:25]([O:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[N:26][CH:27]=1)([O-:21])=[O:20].ClC(Cl)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>[OH-].[Na+]>[CH:13]1([CH:2]([NH:1][CH2:35][C:23]2[C:22]([N+:19]([O-:21])=[O:20])=[CH:27][N:26]=[C:25]([O:28][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH:24]=2)[CH2:3][C:4]([NH:6][CH2:7][CH2:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:5])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1

Komponenten

6

Edukt 4

HCID 63651,1-DichloroethaneHCID 5049666Sodium triacetoxyborohydrideHCID 576783284-Formyl-5-nitro-2-phenoxypyridineHCID 670237583-Amino-3-cyclohexyl-N-(3,3-dimethyl-butyl)-propionamide

Produkt 1

HCID 670235503-Cyclohexyl-N-(3,3-dimethyl-butyl)-3-[(5-nitro-2-phenoxy-pyridin-4-ylmethyl)-amino]-propionamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

A mixture 3-amino-3-cyclohexyl-N-(3,3-dimethyl-butyl)-propionamide (0.57 g, 2.24 mmol), 5-nitro-2-phenoxy-pyridine-4-carbaldehyde (0.57 g, 2.35 mmol), and dichloroethane (100 mL) was stirred for 12 hrs. Sodium triacetoxyborohydride (1.09 g, 5.15 mmol) was added and the resulting mixture was stirred 4 hours at room temperature. Sodium hydroxide solution ([0.1N], 100 mL) was added, the organic layer was separated, treated with MgSO4, filtered and the solvent evaporated under reduced pressure to yield an oil. The oil was purified by column chromatography (10%-40% ethyl acetate/heptane) to yield a residue.

Aufarbeitung

  1. customthe organic layer was separated
  2. additiontreated with MgSO4
  3. filtrationfiltered
  4. customthe solvent evaporated under reduced pressure
  5. customto yield an oil
  6. customThe oil was purified by column chromatography (10%-40% ethyl acetate/heptane)
  7. customto yield a residue

Quellen und Nachweise

ORD-Eintrag
ord-60324abc090d432a90be748da0c0d905
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07531545B2

Notizen zur Reaktion

Wird geladen…