HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 4-(2-(5-((Tert-butoxycarbonylamino)methyl)pyridin-2-ylamino)thiazol-5-ylthio)-3-fluoropicolinic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Methyl 4-(2-(5-((tert-butoxycarbonylamino)methyl)pyridin-2-ylamino)thiazol-5-ylthio)-3-fluoropicolinate | HCID 59200482 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 4-(2-(5-((Tert-butoxycarbonylamino)methyl)pyridin-2-ylamino)thiazol-5-ylthio)-3-fluoropicolinic acid | HCID 59200404 | 87% |
Reaction Steps
A solution of methyl 4-(2-(5-((tert-butoxycarbonylamino)methyl)pyridin-2-ylamino)thiazol-5-ylthio)-3-fluoropicolinate (1.28 g, 2.60 mmol) in tetrahydrofuran (40 mL) was treated with sodium hydroxide (5N, 3.12 mL, 15.6 mmol) at 23° C. The reaction was stirred for 2 hours, then acidified with conc. HCl to pH ˜2.0. Water was then added and the aqueous phase was extracted with ethyl acetate/THF. The combined organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated to give the title material (1.08 g, 87%) as a solid which was used as such in the next reaction.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08148400B2 |
| Source dataset | uspto-grants-2012_04 |
| ORD ID | ord-f937941bd73b4ee3ae3f4db29985ab76 |
| Source note | uspto-grants-2012_04 |