Hydrochloric Acid → [2-({[5-(4-Ethylphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}methyl)-3,3-dimethylbutoxy]-acetic acid tert.-butyl ester

HRID 1926946Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1926946
[OH-].[Na+].[CH2:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:19]3[C:18]([O:20][CH2:21][CH:22]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:23][OH:24])=[N:17][CH:16]=[N:15][C:14]=3[O:13][C:12]=2[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:7][CH:6]=1)[CH3:4].[C:35]([O:39][C:40](=[O:43])[CH2:41]Br)([CH3:38])([CH3:37])[CH3:36].Cl>C1(C)C=CC=CC=1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[C:35]([O:39][C:40](=[O:43])[CH2:41][O:24][CH2:23][CH:22]([CH2:21][O:20][C:18]1[C:19]2[C:11]([C:8]3[CH:7]=[CH:6][C:5]([CH2:3][CH3:4])=[CH:10][CH:9]=3)=[C:12]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[O:13][C:14]=2[N:15]=[CH:16][N:17]=1)[C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:38])([CH3:37])[CH3:36]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 79177tert-Butyl bromoacetateHCID 580168362-({[5-(4-Ethylphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}methyl)-3,3-dimethylbutan-1-ol

Produkt 1

HCID 58016779[2-({[5-(4-Ethylphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}methyl)-3,3-dimethylbutoxy]-acetic acid tert.-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 94433Tetrabutylammonium hydrogen sulfateKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Add 0.5 ml of 11.25 N sodium hydroxide solution to a solution of 265 mg (0.62 mmol) 2-({[5-(4-ethylphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}methyl)-3,3-dimethylbutan-1-ol in 10 ml toluene. After adding 21 mg (0.06 mmol) tetra-n-butylammonium hydrogensulphate and 240 mg (1.23 mmol) 2-bromoacetic acid tert.-butyl ester, stir the reaction mixture for 16 h at 70° C. After cooling to room temperature, neutralize with 1 N hydrochloric acid and extract with ethyl acetate. Wash the organic phase with satd. aqueous sodium chloride solution, dry over sodium sulphate, and filter. Concentrate the filtrate by vacuum evaporation. Purify the residue by preparative RP-HPLC (gradient: water/acetonitrile). 170 mg (51% of theor.) of the desired product (racemate) is obtained.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. extractionextract with ethyl acetate
  3. washWash the organic phase with satd
  4. dry with materialaqueous sodium chloride solution, dry over sodium sulphate
  5. filtrationfilter
  6. concentrationConcentrate the filtrate
  7. customby vacuum evaporation
  8. customPurify the residue by preparative RP-HPLC (gradient: water/acetonitrile)

Quellen und Nachweise

ORD-Eintrag
ord-281514177254418296658c5e5966b362
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08183246B2

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