HuagongsheHuagongshe Chemistry Print Report · For research reference only
Lithium Hydroxide → (Z)-(1R,4R,6S,16R,18R)-14-tert-Butoxycarbonylamino-18-(7-methoxy-2-phenyl-quinolin-4-yloxy)-2,15-dioxo-3,14-diaza-tricyclo[14.3.0.04.6]nonadec-7-ene-4-carboxylic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Lithium Hydroxide | HCID 3939 | — |
| Reactant | (Z)-(1R,4R,6S,16R,18R)-14-tert-Butoxycarbonylamino-18-(7-methoxy-2-phenyl-quinolin-4-yloxy)-2,15-dioxo-3,14-diaza-tricyclo[14.3.0.04,6]nonadec-7-ene-4-carboxylic acid ethyl ester | HCID 11343098 | — |
| Solvent | Methanol tetrahydrofuran water | HCID 21892291 | — |
| Product | (Z)-(1R,4R,6S,16R,18R)-14-tert-Butoxycarbonylamino-18-(7-methoxy-2-phenyl-quinolin-4-yloxy)-2,15-dioxo-3,14-diaza-tricyclo[14.3.0.04.6]nonadec-7-ene-4-carboxylic acid | HCID 11320008 | 46.4% |
Reaction Steps
To a solution of 49 (27 mg, 0.037 mmol) in THF/MeOH/H2O 2:1:1 (5 mL) was added 1 M LiOH (300 μL, 0.300 mmol). The solution was stirred for 24 h at room temperature and finally for one hour at reflux. After acidification to pH 3-4 with 1 M HCl and evaporation the residue was purified by HPLC (MeOH/H2O 80:20 and MeOH/H2O 90:10) providing 50 (12 mg, 46%) as a colorless solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07671032B2 |
| Source dataset | uspto-grants-2010_03 |
| ORD ID | ord-daac0596651c43d8b6bd0dd61ae1f53f |
| Source note | uspto-grants-2010_03 |