HuagongsheHuagongshe Chemistry Print Report · For research reference only
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
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Hydroxide | HCID 14797 | — |
| Reactant | 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 | HCID 66630574 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Water | HCID 962 | — |
| Product | 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 | HCID 66631039 | — |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08318750B2 |
| Source dataset | uspto-grants-2012_11 |
| ORD ID | ord-a5cf2d579d1c4fddb0f4ea2204b048e5 |
| Source note | uspto-grants-2012_11 |