Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Lithium hydroxide, monohydrate | HCID 168937 | — |
| Reactant | Oxolane--water (1/1) | HCID 21881883 | — |
| Reactant | Methyl (1aR,5S,8S,10R,22aR)-5-(1,1-dimethylethyl)-1,1a,3,4,5,6,9,10,18,19,20,21,22,22a-tetradecahydro-14-methoxy-3,6-dioxo-8H-7,10-methanocyclopropa[18,19][1,10,3,6]dioxadiazacyclononadecino[11,12-b]quinoxaline-8-carboxylate | HCID 67304190 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | MK-5172 | HCID 46930991 | 98% |
Reaction Steps
A solution (0.1 M) of methyl (1aR,5S,8S,10R,22aR)-5-tert-butyl-14-methoxy-3,6-dioxo-1,1a,3,4,5,6,9,10,18,19,20,21,22,22a-tetradecahydro-8H-7,10-methanocyclopropa[18,19][1,10,3,6]dioxadiazacyclononadecino[11,12-b]quinoxaline-8-carboxylate in a 1:1 mixture of H2O/THF was treated with LiOH.H2O (3 eq). The resulting mixture was stirred at 20° C. for 18 h, acidified with aqueous HCl (0.2 M) and diluted with EtOAc. The organic phase was separated, washed with aqueous HCl (0.2 M) and brine then dried. Removal of the volatiles afforded the title compound (98%) as a solid. MS (ES+) m/z 555 (M+H)+
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08080654B2 |
|---|
| Source dataset | uspto-grants-2011_12 |
|---|
| ORD ID | ord-e8fb0bceef4742de95d4434d9611bdb2 |
|---|
| Source note | uspto-grants-2011_12 |
|---|
