HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanol → (S)-2-amino-N-(benzo[b]thiophen-3-ylmethyl)-N-((S)-1,1-diethoxypropan-2-yl)propanamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Piperidine | HCID 8082 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | (9H-Fluoren-9-yl)methyl (S)-1-((benzo[b]thiophen-3-ylmethyl)((S)-1,1-diethoxypropan-2-yl)amino)-1-oxopropan-2-ylcarbamate | HCID 86652579 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (S)-2-amino-N-(benzo[b]thiophen-3-ylmethyl)-N-((S)-1,1-diethoxypropan-2-yl)propanamide | HCID 67075261 | 75.2% |
Reaction Steps
(9H-Fluoren-9-yl)methyl (S)-1-((benzo[b]thiophen-3-ylmethyl)((S)-1,1-diethoxypropan-2-yl)amino)-1-oxopropan-2-ylcarbamate (Compound III-12) 15.8 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 7.4 g, (yield 75%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09193734B2 |
| Source dataset | uspto-grants-2015_11 |
| ORD ID | ord-f3654a3c3ba0446e815cab133ae09437 |
| Source note | uspto-grants-2015_11 |