HCID 178450806, Verbindung → HCID 178524866, Verbindung

HRID 2169314Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2169314
C([O:5][C:6]([C:8]1[C:13]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:12]([OH:22])[N:11]=[C:10]([CH2:23][C:24]2([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:28][CH2:27][CH2:26][CH2:25]2)[N:9]=1)=[O:7])(C)(C)C>O1CCCC1.O>[CH2:15]([O:14][C:13]1[C:8]([C:6]([OH:7])=[O:5])=[N:9][C:10]([CH2:23][C:24]2([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:25][CH2:26][CH2:27][CH2:28]2)=[N:11][C:12]=1[OH:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Komponenten

3

Edukt 1

HCID 178450806HCID 178450806, Verbindung

Produkt 1

HCID 178524866HCID 178524866, VerbindungAusbeute 55,44 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21881883Oxolane--water (1/1)Lösungsmittel

Versuchsvorschrift

To a stirred solution of 5-benzyloxy-6-hydroxy-2-(1-phenyl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid tert-butyl ester (282) (1.6 g. 3.48 mmol) in a mixture of tetrahydrofuran:water (2:1) (90 mL), was added lithium-hydroxide monohydrate (2.9 g, 69.57 mmol) and the reaction mixture was refluxed for 18 h. After completion of the reaction, all volatiles were evaporated, added water (30 mL) and washed with ethyl acetate (2×20 mL) to remove non acidic impurities. The separated aqueous part was acidified with 1N HCl to reach a pH of about 5 to 6. The acidified aqueous part was extracted with ethyl acetate (4×50 mL), dried and concentrated to get 5-benzyloxy-6-hydroxy-2-(1-phenyl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid (283) (780 mg, 55.44%) as a white solid.

Aufarbeitung

  1. additionwas added lithium-hydroxide monohydrate (2.9 g, 69.57 mmol)
  2. temperaturethe reaction mixture was refluxed for 18 h
  3. customAfter completion of the reaction
  4. customall volatiles were evaporated
  5. additionadded water (30 mL)
  6. washwashed with ethyl acetate (2×20 mL)
  7. customto remove non acidic impurities
  8. extractionThe acidified aqueous part was extracted with ethyl acetate (4×50 mL)
  9. customdried
  10. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-e544742fce6c47179f410d7d7c59ea15
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09045486B2

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