Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 1,4-Dioxane | HCID 31275 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 2733084 | — |
| Reactant | (5R,9R)-9-(dodecanoyloxy)-1-(9H-fluoren-9-yl)-3,12-dioxo-2,11-dioxa-7-thia-4-azatricosane-5-carboxylic acid | HCID 67414703 | — |
| Reactant | HCID 86678283 | HCID 86678283 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 86678284 | HCID 86678284 | — |
Reaction Steps
To a solution of (S)-tert-butyl 1-(3-(diethoxyphosphoryl)propoxy)propan-2-ylcarbamate (1.3 eq, from the previous step) in DCM (0.22 M) at room temperature was added a solution of 4 M HCl in dioxane (20 eq). The reaction was stirred for 1.5 hours. The reaction mixture was concentrated en vaccuo to give an oil which was evaporated under high vacuum briefly. This residue was taken up in DCM (0.1M). To this solution was added (5R,9R)-9-(dodecanoyloxy)-1-(9H-fluoren-9-yl)-3,12-dioxo-2,11-dioxa-7-thia-4-azatricosane-5-carboxylic acid (6, 1 eq), HBTU (1.2 eq), and DIEA (4 eq). The reaction was stirred at room temperature for 2 hours. The mixture was purified by flash chromatography on a COMBIFLASH® system (ISCO) using a gradient of 0-100% ethyl acetate in hexanes and then 100% ethyl acetate to give the product as an oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08808703B2 |
|---|
| Source dataset | uspto-grants-2014_08 |
|---|
| ORD ID | ord-f68b2061c943434bbfc9592b23d00a47 |
|---|
| Source note | uspto-grants-2014_08 |
|---|
