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

HRID 860058

Reaktionsgleichung

Reaktionsgleichung von HRID 860058
[CH3:1][O:2][C:3]1[CH:30]=[CH:29][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:27]=CN=CN=3)[CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.C(O)(=O)CC.Cl.[Cl-].[Na+].O.[C:40]([CH3:50])(OCC)([O:44]CC)[O:41][CH2:42][CH3:43]>>[CH2:42]([O:41][C:40](=[O:44])[CH2:50][CH:21]([C:22]1[CH:27]=[N:14][CH:9]=[N:8][CH:7]=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:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:30][CH:29]=2)[N:14]=1)[CH3:43]

Komponenten

5

Edukt 4

HCID 1032Propionic AcidHCID 66221Triethyl orthoacetate2×HCID 696671037-[6-(4-Methoxy-benzylamino)-pyridin-2-yl]-1-pyrimidin-4-yl-hept-1-en-3-olHCID 131718760Hydrochloric acid brine

Produkt 1

HCID 69666458(+)9-[6-(4-Methoxy-benzylamino)-pyridin-2-yl]-3-pyrimidin-5-yl-non-4-enoic acid ethyl ester

Versuchsvorschrift

A solution of the allylic alcohol 6-9 (1.6 g, 3.37 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 (5% MeOH/CHCl3) to give 2.01 g of 6-10.

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 (5% MeOH/CHCl3)

Quellen und Nachweise

ORD-Eintrag
ord-2352c1dc79714350a1f67a13705d324a
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07153862B2

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