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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 718932Generated: October 27, 2026

Methanol → (S)-2-amino-N1-(benzo[b]thiophen-3-ylmethyl)-N1-((S)-1,1-diethoxy-propan-2-yl)-N4-tritylsuccinamide

https://huagongshe.com/reaction/718932

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethanolHCID 887—
ReactantPiperidineHCID 8082—
ReactantEthyl AcetateHCID 8857—
Reactant(9H-Fluoren-9-yl)methyl(S)-1-((benzo[b]thiophen-3-ylmethyl)((S)-1,1-diethoxypropan-2-yl)amino)-1,4-dioxo-4-(tritylamino)butan-2-ylcarbamateHCID 131730614—
SolventDichloromethaneHCID 6344—
Product(S)-2-amino-N1-(benzo[b]thiophen-3-ylmethyl)-N1-((S)-1,1-diethoxy-propan-2-yl)-N4-tritylsuccinamideHCID 6707502186.1%

Reaction Steps

(9H-Fluoren-9-yl)methyl (S)-1-((benzo[b]thiophen-3-ylmethyl)((S)-1,1-diethoxypropan-2-yl)amino)-1,4-dioxo-4-(tritylamino)butan-2-ylcarbamate (Compound III-21) 23.5 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 15.1 g, (yield 86%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09193734B2
Source datasetuspto-grants-2015_11
ORD IDord-7a111c72829d456cbd8a0da7d7e71311
Source noteuspto-grants-2015_11