HuagongsheHuagongshe Chemistry Print Report · For research reference only
Lithium Hydroxide → (2-Methyl-4-{methyl-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethyl]-amino}-phenoxy)-acetic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Lithium Hydroxide | HCID 3939 | — |
| Reactant | Potassium bisulfate | HCID 516920 | — |
| Reactant | (2-Methyl-4-{methyl-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethyl]-amino}-phenoxy)-acetic acid ethyl ester | HCID 69217871 | — |
| Solvent | Tetrahydrofuran ethanol | HCID 21873804 | — |
| Product | (2-Methyl-4-{methyl-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethyl]-amino}-phenoxy)-acetic acid | HCID 11465092 | 82.2% |
Reaction Steps
A solution of crude (2-methyl-4-{methyl-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethyl]-amino}-phenoxy)-acetic acid ethyl ester (0.84 g containing 0.74 g, 1.54 mmol) in THF/EtOH (9.2 ml, 1:1) were treated at 0° C. with 1M LiOH (4.6 ml, 4.6 mmol) for 2 min. After 2 h at RT, the solution was acidified by adding aqueous 10% KHSO4, and the mixture was extracted with Et2O (3×). The organic phase was washed with aqueous 10% NaCl, dried over Na2SO4 and evaporated. Crystallization (CH2Cl2/Et2O) gave 0.57 g (82%) (2-methyl-4-{methyl-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethyl]-amino}-phenoxy)-acetic acid as light yellow powder, MS: 449 (M-H)−, MP: 146-149° C., dec.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07345067B2 |
| Source dataset | uspto-grants-2008_03 |
| ORD ID | ord-426a9e11d1ea494da3b68d746ba5357e |
| Source note | uspto-grants-2008_03 |