HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → n-((5s)-3-(4-(2s-(Pyrimidin-2-yl)thiomethyl-2,5-dihydropyrrol-4-yl)phenyl)-2-oxooxazolidin-5-ylmethyl)acetamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Acetone hydrogen chloride | HCID 19044839 | — |
| Reactant | n-((5s)-3-(4-(2s-(Pyrimidin-2-yl)thiomethyl-1-trityl-2,5-dihydropyrrol-4-yl)phenyl)-2-oxooxazolidin-5-ylmethyl)acetamide | HCID 69997770 | — |
| Solvent | Acetone | HCID 180 | — |
| Solvent | Water | HCID 962 | — |
| Product | n-((5s)-3-(4-(2s-(Pyrimidin-2-yl)thiomethyl-2,5-dihydropyrrol-4-yl)phenyl)-2-oxooxazolidin-5-ylmethyl)acetamide | HCID 69998857 | 92% |
Reaction Steps
The N-trityl compound (Example 30, 0.528 g, 0.79 mM) in acetone (8 ml) at 0° C. was treated with freshly prepared HCl/acetone (4 ml) and stirred. The mixture was periodically treated with 10% HCl in water until TLC indicated consumption of starting material. The reaction mixture was then diluted with EtOAc (30 ml) and taken to pH 11 with NH4OH solution. The aqueous layer was extracted with EtOAc and the combined organics dried (MgSO4) and evaporated to a residue which was triturated with diethyl ether to give the title amine (0.309 g, 92%) which was used without further purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06605630B1 |
| Source dataset | uspto-grants-2003_08 |
| ORD ID | ord-0030985c8ff84c79b30fcf1ac4e763f2 |
| Source note | uspto-grants-2003_08 |