HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → HCID 118252502, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | N-(tert-Butoxycarbonyl)-L-cyclohexylglycine | HCID 7004938 | — |
| 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 131736758 | HCID 131736758 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 118252502 | HCID 118252502 | 82.2% |
Reaction Steps
To a solution of (S)-2,3-dihydro-1H-isoindole-1-carboxylic acid (2,6-difluoro-phenyl)-amide (160 mg, 412 μmol, Eq: 1.00), (S)-2-(tert-butoxycarbonylamino)-2-cyclohexylacetic acid (106 mg, 412 μmol, Eq: 1.00) and HATU (172 mg, 453 μmol, Eq: 1.1) in DMF (500 μL) at 0° C. was added DIEA (160 mg, 216 μL, 1.24 mmol, Eq: 3). The reaction was stirred at RT for 1 h, diluted with water and extracted with EtOAc. The combined organics were washed with water, brine, dried with MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography to give {(S)-1-cyclohexyl-2-[(S)-1-(2,6-difluoro-phenyl-carbamoyl)-1,3-dihydro-isoindol-2-yl]-2-oxo-ethyl}-carbamic acid tert-butyl ester (174 mg) as a white foam.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09422332B2 |
| Source dataset | uspto-grants-2016_08 |
| ORD ID | ord-aec712656b184f1e84e5f738b9eae0a9 |
| Source note | uspto-grants-2016_08 |