HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → (2S,3R)-2-hydroxy-3-{3-[4-(trifluoromethoxy)phenyl]propyl}butanedioic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Potassium Hydroxide | HCID 14797 | — |
| Reactant | diisopropyl (2S,3R)-2-hydroxy-3-{3-[4-(trifluoromethoxy)phenyl]propyl}butanedioate | HCID 58487998 | — |
| Solvent | Oxolane--water (1/1) | HCID 21881883 | — |
| Product | (2S,3R)-2-hydroxy-3-{3-[4-(trifluoromethoxy)phenyl]propyl}butanedioic acid | HCID 58487990 | 110.9% |
Reaction Steps
To a solution of diisopropyl (2S,3R)-2-hydroxy-3-{3-[4-(trifluoromethoxy)phenyl]propyl}butanedioate (6.98 g; 16.6 mmol; 1.0 eq.) in THF/water (3/1; 140 mL) was added potassium hydroxide (5.59 g; 99.6 mmol; 6.0 eq.). The reaction mixture was then stirred for 14 h at RT. The aq. layers were acidified with an aqueous solution of HCl to pH 2, extracted with EtOAc. The combined organic layers were then dried over MgSO4 and evaporated to give the title compound as an oil (6.19 g), used in the next steps without further purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08247437B2 |
| Source dataset | uspto-grants-2012_08 |
| ORD ID | ord-b4339f150c964837b0dec952608075ce |
| Source note | uspto-grants-2012_08 |