HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → tert-Butyl 1-(3-{[(2S)-2-cyclopentyl-2-(4-methylphenyl)acetyl]amino}benzyl)cyclopropane-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| 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 | (2S)-Cyclopentyl-(4-methylphenyl)acetic acid | HCID 28293121 | — |
| Reactant | tert-Butyl 1-(3-aminobenzyl)cyclopropanecarboxylate | HCID 58136514 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | tert-Butyl 1-(3-{[(2S)-2-cyclopentyl-2-(4-methylphenyl)acetyl]amino}benzyl)cyclopropane-carboxylate | HCID 68006853 | — |
Reaction Steps
At RT, 453 mg (1191 μmol) of HATU and 479 μl (2750 μmol) of N,N-diisopropylethylamine were added to a solution of 200 mg (916 μmol) of (+)-(2S)-cyclopentyl(4-methylphenyl)acetic acid in 1 ml of DMF. The mixture was stirred for 30 min. 249 mg (1008 μmol) of tert-butyl 1-(3-aminobenzyl)cyclopropanecarboxylate were then added. The reaction mixture was stirred overnight and then directly separated into its components by preparative HPLC. This gave 328 mg (80% of theory) of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09018258B2 |
| Source dataset | uspto-grants-2015_04 |
| ORD ID | ord-2bbd946e32d1453984a7954c15a4a0c7 |
| Source note | uspto-grants-2015_04 |