HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → Boc-Aze-NHCH2-Ph
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate | HCID 2733207 | — |
| Reactant | (2S)-1-((tert-butoxy)carbonyl)azetidine-2-carboxylic acid | HCID 2734495 | — |
| Reactant | 4-Aminomethyl-2-fluoro-benzonitrile | HCID 21904652 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | Boc-Aze-NHCH2-Ph | HCID 91021871 | 100.8% |
Reaction Steps
To an ice cooled solution of Boc-Aze-OH (0.194 g, 0.96 mmol) in 5 mL of DMF was added TBTU (0.50 g, 9.6 mmol). After 30 min another solution, comprising 4-aminomethyl-2-fluorobenzonitrile (0.17 g, 0.81 mmol; see step (v) above) and diisopropylethyl amine (0.326 g, 2.53 mmol) in 7 mL of DMF was added. The resulting solution was stirred overnight at room temperature. The solvent was evaporated and the product was purified by preparative RPLC using CH3CN:0.1M NH4OAc (50:50). Freeze-drying gave 0.237 g (74%) of the desired sub-title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07645751B2 |
| Source dataset | uspto-grants-2010_01 |
| ORD ID | ord-600a3eda5404444db9c1a24a1a22af2a |
| Source note | uspto-grants-2010_01 |