HuagongsheHuagongshe Chemistry Print Report · For research reference only
Fluocortolone → (2S)-2-((1,1-dimethylethoxycarbonyl)-amino)-3-methyl-butyric acid [11beta,21-dihydroxy-6alpha-fluoro-16alpha-methyl-3,20-dioxo-pregna-1,4-dien-21-yl] ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Fluocortolone | HCID 9053 | — |
| Reactant | Dicyclohexylcarbodiimide | HCID 10868 | — |
| 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-6alpha-fluoro-16alpha-methyl-3,20-dioxo-pregna-1,4-dien-21-yl] ester | HCID 131719962 | 46% |
Reaction Steps
26 mmol of fluocortolone (FC) is reacted with 32 mmol of Boc-valine (Boc-Val-OH), 2.9 mmol of 4-dimethylaminopyridine and 34 mmol of dicyclohexylcarbodiimide in dichloromethane/dioxane 3:2. Chromatography (ethyl acetate/hexane 2:1): F1 9.3 g of pure product, F2 4.8 g of slightly contaminated product. (Total yield 92%) crystallization of F1 from ethyl acetate/hexane yields 7.0 g (46%) of (2S)-2-((1,1-dimethylethoxycarbonyl)-amino)-3-methyl-butyric acid [11β,21-dihydroxy-6α-fluoro-16α-methyl-3,20-dioxo-pregna-1,4-dien-21-yl] ester.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05616573 |
| Source dataset | uspto-grants-1997_04 |
| ORD ID | ord-6c63a7b0bcdf4386a1182731aa9a9a7e |
| Source note | uspto-grants-1997_04 |