HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2205058Generated: November 4, 2026
Octyl isocyanate → (R)-tert-butyl 2-(benzyloxycarbonylamino)-3-((R)-2,3-bis(octylcarbamoyloxy)propylthio)propanoate
https://huagongshe.com/reaction/2205058
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Octyl isocyanate | HCID 76616 | — |
| Reactant | (R)-tert-butyl 2-(benzyloxycarbonylamino)-3-((R)-2,3-dihydroxypropylthio)propanoate | HCID 67400883 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Benzene | HCID 241 | — |
| Product | (R)-tert-butyl 2-(benzyloxycarbonylamino)-3-((R)-2,3-bis(octylcarbamoyloxy)propylthio)propanoate | HCID 71294581 | — |
Reaction Steps
A solution of (R)-tert-butyl 2-(benzyloxycarbonylamino)-3-((R)-2,3-dihydroxypropylthio)propanoate (13) was stirred in anhydrous benzene (0.1 M) under nitrogen at room temperature. Octyl isocyanate (2.02 eq) and DMAP (dimethylaminopyridine, 2.02 eq) were added and the resulting mixture heated to 40° C. and stirred overnight. The reaction mixture was concentrated to remove benzene then reconstituted in DCM and purified by flash chromatography on a COMBIFLASH® system (ISCO) using a gradient of 0-50% EtOAc/Hex to afford the title product as a colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09365506B2 |
|---|
| Source dataset | uspto-grants-2016_06 |
|---|
| ORD ID | ord-2f824df1fff14cc0bb999fa0b1728316 |
|---|
| Source note | uspto-grants-2016_06 |
|---|
