HuagongsheHuagongshe Chemistry Print Report · For research reference only
Lithium hydroxide, monohydrate → 4-(4-(2-Tert-butoxy-2-oxoethyl)-2-(methylsulfonamido-methyl)phenoxy)benzoic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Lithium hydroxide, monohydrate | HCID 168937 | — |
| Reactant | Methyl 4-(4-(2-tert-butoxy-2-oxoethyl)-2-(methylsulfonamidomethyl)phenoxy)benzoate | HCID 68468952 | — |
| Solvent | Hydrochloric Acid | HCID 313 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 4-(4-(2-Tert-butoxy-2-oxoethyl)-2-(methylsulfonamido-methyl)phenoxy)benzoic acid | HCID 68464598 | 81.5% |
Reaction Steps
The product of step C (900 mg, 2.00 mmol) was diluted with dioxane (10 mL) followed by the addition of LiOH—H2O (126 mg, 3.00 mmol) dissolved in water (2 mL). After stirring for 12 hours, the reaction mixture was diluted with ethyl acetate and 2N HCl. The layers were separated and the organic layer was dried over MgSO4, filtered and concentrated. The material was purified using a biotage 40M cartridge eluting with methylene chloride:MeOH (95:5) to yield 4-(4-(2-tert-butoxy-2-oxoethyl)-2-(methylsulfonamido-methyl)phenoxy)benzoic acid (710 mg, 81.4% yield) as a clear oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08492437B2 |
| Source dataset | uspto-grants-2013_07 |
| ORD ID | ord-8689a0edd1d3482fb11a0144e5b99917 |
| Source note | uspto-grants-2013_07 |