HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 3-(3-(tert-butylthio)-1-(4-chlorobenzyl)-5-(pyridin-2-ylmethoxy)-1H-indol-2-yl)-2,2-dimethylpropanoic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Methanol | HCID 887 | — |
| Reactant | Lithium Hydroxide | HCID 3939 | — |
| Reactant | 3-[1-(4-Chlorobenzyl)-3-(t-butylthio)-5-(pyridin-2-ylmethyoxy)indol-2-yl]-2,2-dimethylpropanoic acid allyl ester | HCID 15229441 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 3-(3-(tert-butylthio)-1-(4-chlorobenzyl)-5-(pyridin-2-ylmethoxy)-1H-indol-2-yl)-2,2-dimethylpropanoic acid | HCID 9828630 | — |
Reaction Steps
The compound from Step 1 (133 mg) was dissolved in THF (5 mL), MeOH (3 mL), and 1N LiOH (1.2 mL) and heated at 55° C. for 1 hour. After cooling to room temperature, the mixture was acidified with 1N HCl and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered, and evaporated to dryness. The residue was swished in ether/hexane, affording the title compound as a white solid, m.p. 186.2°-187.7° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05389650 |
| Source dataset | uspto-grants-1995_02 |
| ORD ID | ord-3b3f223e6a3d453a8769b4920cc904fe |
| Source note | uspto-grants-1995_02 |