HuagongsheHuagongshe Chemistry Print Report · For research reference only
dimethylsulfoxide THF → (+)-1-(4-{2-[2-(4-Chloro-phenyl)-4,5,6,7-tetrahydro-2H-indazol-3-yl]-2-cyclohexyl-acetylamino}-3-fluoro-phenoxy)-cyclopropanecarboxylic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | dimethylsulfoxide THF | HCID 21830753 | — |
| Reactant | (+)-1-(4-{2-[2-(4-chloro-phenyl)-4,5,6,7-tetrahydro-2H-indazol-3-yl]-2-cyclohexyl-acetylamino}-3-fluoro-phenoxy)-cyclopropanecarboxylic acid tert-butyl ester | HCID 67130978 | — |
| Solvent | Formic Acid | HCID 284 | — |
| Solvent | Isopropanol | HCID 3776 | — |
| Product | (+)-1-(4-{2-[2-(4-Chloro-phenyl)-4,5,6,7-tetrahydro-2H-indazol-3-yl]-2-cyclohexyl-acetylamino}-3-fluoro-phenoxy)-cyclopropanecarboxylic acid | HCID 45110644 | 100% |
Reaction Steps
A solution of (+)-1-(4-{2-[2-(4-chloro-phenyl)-4,5,6,7-tetrahydro-2H-indazol-3-yl]-2-cyclohexyl-acetylamino}-3-fluoro-phenoxy)-cyclopropanecarboxylic acid tert-butyl ester (22 mg, 35 umol; example 21.5) in isopropanol (200 ul) and formic acid (400 ul) was stirred at 90° C. for 2 h. The mixture was poured onto ice water/brine 1/1 and extracted two times with iPrOAc. The combined extracts were washed with ice water/brine 1/1 and dried over Na2SO4. After filtration the solvent was removed under reduced pressure to give the title compound (20 mg, 35 umol; quant; 100% ee) as yellow foam. MS: m/e=566.3 [M+H+].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08008505B2 |
| Source dataset | uspto-grants-2011_08 |
| ORD ID | ord-8852ad3059344f719c7c6143278516da |
| Source note | uspto-grants-2011_08 |