HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanol → tert-butyl (S)-5-amino-6-(((S)-1,1-diethoxypropan-2-yl)(naphthalen-1-ylmethyl)amino)-6-oxohexylcarbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Piperidine | HCID 8082 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | 6-tert-butoxycarbonylamino-2-(S)-(9H-fluoren-9-yl)methylamino-N-((S)-1,1-diethoxypropan-2-yl)-N-(naphthalen-1-ylmethyl)hexanamide | HCID 67088756 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | tert-butyl (S)-5-amino-6-(((S)-1,1-diethoxypropan-2-yl)(naphthalen-1-ylmethyl)amino)-6-oxohexylcarbamate | HCID 86698537 | 80% |
Reaction Steps
6-tert-butoxycarbonylamino-2-(S)-(9H-fluoren-9-yl)methylamino-N—((S)-1,1-diethoxypropan-2-yl)-N-(naphthalen-1-ylmethyl)hexanamide (Compound III-13) 19.9 g (27 mmol) and piperidine 22.7 g (270 mmol) were added in DCM (90 ml). The mixture was stirred for 1.5 h at room temperature. The mixture was diluted with DCM (200 ml) and washed with water (150 ml×3). The solution was concentrated in vacuo. The residue was purified by column chromatography on silica gel with PE:EA=50:1 to DCM:MeOH=10:1 to give the title compound 11.1 g, (yield 80%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09193734B2 |
| Source dataset | uspto-grants-2015_11 |
| ORD ID | ord-ff7e30db5082427ca9232ad3afba2e0f |
| Source note | uspto-grants-2015_11 |