Potassium Hydroxide → 1-[9-((1R,2S,3R,4S)-2,3-Dihydroxy-4-propionylamino-cyclopentyl)-6-(2,2-diphenyl-ethylamino)-9H-purin-2-yl]-1H-pyrazole-4-carboxylic acid

HRID 1882639Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1882639
C([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:11]2[N:19]=[C:18]3[C:14]([N:15]=[CH:16][N:17]3[C@@H:20]3[CH2:24][C@H:23]([NH:25][C:26](=[O:29])[CH2:27][CH3:28])[C@@H:22]([OH:30])[C@H:21]3[OH:31])=[C:13]([NH:32][CH2:33][CH:34]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[N:12]=2)[CH:10]=1)=[O:5])C.[OH-].[K+]>O.CO>[OH:31][C@@H:21]1[C@H:22]([OH:30])[C@@H:23]([NH:25][C:26](=[O:29])[CH2:27][CH3:28])[CH2:24][C@H:20]1[N:17]1[CH:16]=[N:15][C:14]2[C:18]1=[N:19][C:11]([N:9]1[CH:10]=[C:6]([C:4]([OH:5])=[O:3])[CH:7]=[N:8]1)=[N:12][C:13]=2[NH:32][CH2:33][CH:34]([C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Komponenten

5

Edukt 2

HCID 14797Potassium HydroxideHCID 666305741-[9-((1R,2S,3R,4S)-2,3-Dihydroxy-4-propionylamino-cyclopentyl)-6-(2,2-diphenyl-ethylamino)-9H-purin-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester

Produkt 1

HCID 666310391-[9-((1R,2S,3R,4S)-2,3-Dihydroxy-4-propionylamino-cyclopentyl)-6-(2,2-diphenyl-ethylamino)-9H-purin-2-yl]-1H-pyrazole-4-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution comprising 1-[9-((1R,2S,3R,4S)-2,3-dihydroxy-4-propionylamino-cyclopentyl)-6-(2,2-diphenyl-ethylamino)-9H-purin-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester (Example 173 step 1) (0.4 g, 0.64 mmol) in water (3 ml) is treated with 1M KOH in MeOH (6 ml) and stirred at room temperature for 48 h. The solvent is removed in vacuo and the resulting crude product is dissolved in water (5 ml) and acidified to pH 3-4 with 1.5N HCl. The solution is extracted with EtOAc and the organic portion is dried over sodium sulphate and concentrated in vacuo. Purification by chromatography on silica eluting with 5% MeOH in chloroform affords the title compound.

Aufarbeitung

  1. customThe solvent is removed in vacuo
  2. dissolutionthe resulting crude product is dissolved in water (5 ml)
  3. extractionThe solution is extracted with EtOAc
  4. dry with materialthe organic portion is dried over sodium sulphate
  5. concentrationconcentrated in vacuo
  6. customPurification by chromatography on silica eluting with 5% MeOH in chloroform

Quellen und Nachweise

ORD-Eintrag
ord-a5cf2d579d1c4fddb0f4ea2204b048e5
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318750B2

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