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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 718924Generated: October 28, 2026

Methanol → tert-butyl (S)-5-amino-6-(((S)-1,1-diethoxypropan-2-yl)(naphthalen-1-ylmethyl)amino)-6-oxohexylcarbamate

https://huagongshe.com/reaction/718924

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethanolHCID 887—
ReactantPiperidineHCID 8082—
ReactantEthyl AcetateHCID 8857—
Reactant6-tert-butoxycarbonylamino-2-(S)-(9H-fluoren-9-yl)methylamino-N-((S)-1,1-diethoxypropan-2-yl)-N-(naphthalen-1-ylmethyl)hexanamideHCID 67088756—
SolventDichloromethaneHCID 6344—
Producttert-butyl (S)-5-amino-6-(((S)-1,1-diethoxypropan-2-yl)(naphthalen-1-ylmethyl)amino)-6-oxohexylcarbamateHCID 8669853780%

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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09193734B2
Source datasetuspto-grants-2015_11
ORD IDord-ff7e30db5082427ca9232ad3afba2e0f
Source noteuspto-grants-2015_11