HuagongsheHuagongshe Chemistry Print Report · For research reference only
Pyrrolidine → HCID 69287228, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Pyrrolidine | HCID 31268 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | HCID 69285545 | HCID 69285545 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 69287228 | HCID 69287228 | 71.1% |
Reaction Steps
To a solution of (1R,2S,5R)-2-benzyloxycarbonylamino-5-tert-butoxycarbonylamino-cyclohexanecarboxylic acid (240 mg, 0.6 mmol) in DMF (15 mL) at rt was added HATU (278 mg, 0.73 mmol), pyrrolidine (0.06 mL, 0.73 mmol), and iPr2NEt (0.13 mL, 0.73 mmol). The mixture was stirred at rt for 16 h before water and EtOAc were added. The organic layer was separated and re-washed twice before it was collected, dried over Na2SO4, and concentrated to provide (1S,2R,4R)-[4-tert-butoxycarbonylamino-2-(pyrrolidine-1-carbonyl)-cyclohexyl]-carbamic acid benzyl ester as a glassy solid (190 mg, 69%). MS found: (M+H)+=446.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07378409B2 |
| Source dataset | uspto-grants-2008_05 |
| ORD ID | ord-56b043036d514aaf829a9614a162f8ce |
| Source note | uspto-grants-2008_05 |