HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium borohydride → Obeticholic Acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | (R)-4-((3R,5S,6R,8S,9S,10S,13R,14S,17R)-6-ethyl-3-hydroxy-10,13-dimethyl-7-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid | HCID 67102585 | — |
| Product | Obeticholic Acid | HCID 447715 | — |
Reaction Steps
Step 6 is the reaction of 3α-hydroxy-6α-ethyl-7-keto-5β-cholan-24-oic acid (6) with NaBH4 to form crystalline obeticholic acid. In one embodiment, Step 6 is carried out at a temperature at about 85° C. to about 110° C. in a basic aqueous solution. In one embodiment, the temperature is about 90° C. to about 95° C. In one embodiment, the basic aqueous solution is an aqueous NaOH solution. In one embodiment, the basic aqueous solution is a mixture of 50% wt. NaOH solution and water. In one embodiment, the reaction mixture of compound 6 and NaBH4 was stirred for about 3 hours to about 5 hours. In another embodiment, the reaction mixture was stirred for about 4 hours.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09238673B2 |
| Source dataset | uspto-grants-2016_01 |
| ORD ID | ord-ad276044cf4445e49d77cb5a1199f690 |
| Source note | uspto-grants-2016_01 |