HuagongsheHuagongshe Chemistry Print Report · For research reference only
Betamethasone Valerate → (2S)-2-((1,1-dimethylethoxycarbonyl)-amino)-3-methyl-butyric acid [11beta,21-dihydroxy-3,20-dioxo-9-fluoro-16beta-methyl-17-valeroyloxy-pregna-1,4-dien-21-yl] ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Betamethasone Valerate | HCID 16533 | — |
| Reactant | Boc-L-Valine | HCID 83693 | — |
| Reactant | Ethyl acetate hexane | HCID 21226206 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dioxane methylene chloride | HCID 18626912 | — |
| Product | (2S)-2-((1,1-dimethylethoxycarbonyl)-amino)-3-methyl-butyric acid [11beta,21-dihydroxy-3,20-dioxo-9-fluoro-16beta-methyl-17-valeroyloxy-pregna-1,4-dien-21-yl] ester | HCID 131719966 | 73% |
Reaction Steps
21 mmol of betamethasone-17-valerate is reacted with 25 mmol of Boc-valine (Boc-Val-OH), 2.5 mmol of 4-dimethylaminopyridine and 27 mmol of dicyclohexylcarbodiimidazole in dichloromethane/dioxane 1:1 analogously to Example 1. Chromatography (1. ethyl acetate/hexane 2:1 and 2. ethyl acetate/hexane 1:1) yields 10.1 g (73%) of pure (2S)-2-((1,1-dimethylethoxycarbonyl)-amino)-3-methyl-butyric acid [11β,21-dihydroxy-3,20-dioxo-9-fluoro-16β-methyl-17-valeroyloxy-pregna -1,4-dien-21-yl] ester as foam.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05616573 |
| Source dataset | uspto-grants-1997_04 |
| ORD ID | ord-4aa3a2e7e4c1420a8ea5ecf484c50303 |
| Source note | uspto-grants-1997_04 |