Propionic Acid → (+/-)9-[6-(4-Methoxy-benzylamino)-pyridin-2-yl]-3-(2-methyl-pyrimidin-5-yl)-non-4-enoic acid ethyl ester

HRID 860077

Reaktionsgleichung

Reaktionsgleichung von HRID 860077
[CH3:1][O:2][C:3]1[CH:31]=[CH:30][C:6]([CH2:7][NH:8][C:9]2[N:14]=[C:13]([CH2:15][CH2:16][CH2:17][CH2:18][CH:19](O)[CH:20]=[CH:21][C:22]3[CH:23]=[N:24][C:25]([CH3:28])=[N:26][CH:27]=3)[CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.C(O)(=O)CC.Cl.[Cl-].[Na+].O.[C:41]([CH3:51])(OCC)([O:45]CC)[O:42][CH2:43][CH3:44]>>[CH2:43]([O:42][C:41](=[O:45])[CH2:51][CH:21]([C:22]1[CH:23]=[N:24][C:25]([CH3:28])=[N:26][CH:27]=1)[CH:20]=[CH:19][CH2:18][CH2:17][CH2:16][CH2:15][C:13]1[CH:12]=[CH:11][CH:10]=[C:9]([NH:8][CH2:7][C:6]2[CH:30]=[CH:31][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[N:14]=1)[CH3:44]

Komponenten

5

Edukt 4

HCID 1032Propionic AcidHCID 66221Triethyl orthoacetate2×HCID 696662517-[6-(4-Methoxy-benzylamino)-pyridin-2-yl]-1-(2-methyl-pyrimidin-5-yl)-hept-1-en-3-olHCID 131718760Hydrochloric acid brine

Produkt 1

HCID 69666047(+/-)9-[6-(4-Methoxy-benzylamino)-pyridin-2-yl]-3-(2-methyl-pyrimidin-5-yl)-non-4-enoic acid ethyl esterAusbeute 86 %

Versuchsvorschrift

A solution of the allylic alcohol 16-4 (2.3 g, 5.49 mmol) in (EtO)3CMe (10 mL) was treated with 100 uL of a 1 mL solution of (EtO)3CMe containing 10 uL of propionic acid. The yellow solution was heated at 150° for 90 minutes. The solution was cooled to room temperature and poured into 1N HCl/brine. The mixture was extracted with CHCl3, dried, concentrated, and purified on silica gel (90:5:5 CHCl3:EtOAc:MeOH) to give 2.32 g (86%) of 16-7.

Aufarbeitung

  1. temperatureThe yellow solution was heated at 150° for 90 minutes
  2. extractionThe mixture was extracted with CHCl3
  3. customdried
  4. concentrationconcentrated
  5. custompurified on silica gel (90:5:5 CHCl3:EtOAc:MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-098c08eb2017433d9c93bfdcfee06ce7
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07153862B2

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