HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 3-[1-(4-Chlorobenzyl)-3-(t-butylthio)-5-(2-methylthiazol-4-ylmethoxy)indol-2-yl]-2,2-dimethylpropanoic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Methanol | HCID 887 | — |
| Reactant | Methyl 3-[1-(4-chlorobenzyl)-3-(t-butylthio)-5-(2-methylthiazol-4-ylmethoxy)indol-2-yl]-2,2-dimethylpropanoate | HCID 19097505 | — |
| Solvent | Lithium Hydroxide | HCID 3939 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 3-[1-(4-Chlorobenzyl)-3-(t-butylthio)-5-(2-methylthiazol-4-ylmethoxy)indol-2-yl]-2,2-dimethylpropanoic acid | HCID 19097504 | — |
Reaction Steps
A solution of the ester from Step 1 (22.5 g) in 118 mL 1N LiOH, 120 mL THF, and 65 mL MeOH was heated at 60° C. for 2 hours. The mixture was cooled, poured onto 1N HCl, and extracted with EtOAc (3×). After washing the organic phase twice with brine, the solution was dried (MgSo4) and evaporated. The residue was swished with ether/hexane 1:2 to give the title compound as a solid; m.p. 196.5°-198° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05290798 |
| Source dataset | uspto-grants-1994_03 |
| ORD ID | ord-9c6cf8e6006f4b808bb9d24f0059472c |
| Source note | uspto-grants-1994_03 |