HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Methylmorpholine → N-(tert-butoxycarbonyl)-L-aspartic acid 1-benzyl ester 4-piperidinamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Methylmorpholine | HCID 7972 | — |
| Reactant | Piperidine | HCID 8082 | — |
| Reactant | O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate | HCID 2733207 | — |
| Reactant | (3S)-4-(benzyloxy)-3-(((tert-butoxy)carbonyl)amino)-4-oxobutanoic acid | HCID 7017887 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | N-(tert-butoxycarbonyl)-L-aspartic acid 1-benzyl ester 4-piperidinamide | HCID 70086528 | — |
Reaction Steps
A solution of N-(tert-butoxycarbonyl)-L-aspartic acid 1-benzyl ester (1 g) and piperidine (0.32 mL) in acetonitrile (15 mL) was allowed to react with N-methylmorpholine (0.42 mL) and TBTU (1.2 g) for 6 hr at room temperature. The solvent was removed and the residue, dissolved in EtOAc, was sequentially washed with 2% aqueous hydrochloric acid, saturated aq. NaHCO3 and brine. After drying (Na2SO4) and rotoevaporation, the resulting yellowish oil was purified by flash chromatography over silica to obtain N-(tert-butoxycarbonyl)-L-aspartic acid 1-benzyl ester-4-piperidinamide (900 mg) as a colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06482827B1 |
| Source dataset | uspto-grants-2002_11 |
| ORD ID | ord-60c005376dde4530a849137725f3e1dc |
| Source note | uspto-grants-2002_11 |