HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Methylmorpholine → HCID 86756857, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Methylmorpholine | HCID 7972 | — |
| Reactant | L-Leucinol | HCID 111307 | — |
| Reactant | O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate | HCID 2733207 | — |
| Reactant | (S)-2-((tert-Butoxycarbonyl)amino)-3,3-dimethylbutanoic acid | HCID 2734668 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 86756857 | HCID 86756857 | 80.4% |
Reaction Steps
To a suspension of N-tert-butyloxycarbonyl-L-tert-butylglycine 8 (2.43 g, 10.5 mmol), L-leucinol 9 (1.23 g, 10.5 mmol) and TBTU (3.44 g, 11.5 mmol) in acetonitrile (30 mL) at 0° (ice bath) was added N-methyl morpholine (1.3 mL, 11.5 mmol). The resulting mixture was stirred 19 h (allowing the ice bath to warm to room temperature) and the white solid was collected on a filter (486 mg, 14% yield). The mother liquors were purified by flash chromatography (SiO2, 25-35% EtOAc-hexane) affording N-tert-butyloxycarbonyl-L-tert-butylglycyl-L-leucinol 10 (2.79 g, 80% yield) as a white solid (including the filtered solid).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06239125B1 |
| Source dataset | uspto-grants-2001_05 |
| ORD ID | ord-10d1169fead94d749fb34913eee59801 |
| Source note | uspto-grants-2001_05 |