HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → HCID 14135842, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Methanol | HCID 887 | — |
| Reactant | methyl (4R)-4-[(5R,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-3,6-dioxo-2,4,5,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate | HCID 14135841 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 14135842 | HCID 14135842 | 100% |
Reaction Steps
The 3,6-dioxo-5α sterol was prepared by acid-catalyzed isomerization of the 5β sterol. To methanol (250 ml) was added the 3,6-dioxo-5β sterol 1017 (9.6 g, 24 mmol) and tetrahydrofuran (25 ml) to dissolve the sterol completely. Concentrated hydrochloric acid (12.5 ml) was added, and the reaction was allowed to proceed overnight. The solvent was then removed under vacuum to yield 9.6 g (100% yield) of methyl 3,6-dioxo-5α-cholan-24-oate 1018 (see Organic Preparations and Procedures Int. 19(2-3), 1987, 197-208; authors used base-catalyzed isomerization using sodium methoxide rather than HCl).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05994336 |
| Source dataset | uspto-grants-1999_11 |
| ORD ID | ord-44db2d90d679431c80464bd762a893e6 |
| Source note | uspto-grants-1999_11 |