HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → (Z)-(1S,4R,6S,18R)-18-[2-(4-ethynyl-thiazol-2-yl)-7-methoxy-8-methyl-quinolin-4-yloxy]-13-methyl-2,14-dioxo-3,13,15-triaza-tricyclo[13.4.0.0*4,6*]nonadec-7-ene-4-carboxylic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Lithium Hydroxide | HCID 3939 | — |
| Reactant | (Z)-(1S,4R,6S,18R)-18-[2-(4-ethynyl-thiazol-2-yl)-7-methoxy-8-methyl-quinolin-4-yloxy]-13-methyl-2,14-dioxo-3,13,15-triaza-tricyclo[13.4.0.0*4,6*]nonadec-7-ene-4-carboxylic acid methyl ester | HCID 87472167 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | (Z)-(1S,4R,6S,18R)-18-[2-(4-ethynyl-thiazol-2-yl)-7-methoxy-8-methyl-quinolin-4-yloxy]-13-methyl-2,14-dioxo-3,13,15-triaza-tricyclo[13.4.0.0*4,6*]nonadec-7-ene-4-carboxylic acid | HCID 87472044 | 46% |
Reaction Steps
A mixture of compound 37 (0.11 g, 1 eq.) and LiOH (0.022 g, 5 eq.) in a mixture of tetrahydrofuran (5 mL) and water (5 mL) was stirred at room temperature overnight. HCl (1N) was added and the mixture was extracted with dichloromethane. Dried organics were evaporated in vacuo. The crude residue was purified by chromatography on silica gel to give compound 38 in 46% yield. MS (ESI, EI+) m/z=644 (MH+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08993595B2 |
| Source dataset | uspto-grants-2015_03 |
| ORD ID | ord-ac3975ad8e9c4cc7887e74073da7a7fc |
| Source note | uspto-grants-2015_03 |