HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → (9H-fluoren-9-yl)methyl((14R,18R)-1-(diethoxyphosphoryl)-18-dodecanamido-13-oxo-3,6,9,20-tetraoxa-16-thia-12-azadotriacontan-14-yl)carbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 2733084 | — |
| Reactant | (R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(((R)-2-dodecanamido-3-(dodecyloxy)propyl)thio)propanoic acid | HCID 67402076 | — |
| Reactant | Diethyl 2-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)ethylphosphonate | HCID 86667767 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (9H-fluoren-9-yl)methyl((14R,18R)-1-(diethoxyphosphoryl)-18-dodecanamido-13-oxo-3,6,9,20-tetraoxa-16-thia-12-azadotriacontan-14-yl)carbamate | HCID 86678311 | — |
Reaction Steps
To a solution of (R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(((R)-2-dodecanamido-3-(dodecyloxy)propyl)thio)propanoic acid (1 eq) and HBTU (1.2 eq) in DCM (0.06 M) was added DIEA (3.5 eq), followed by diethyl(2-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)ethyl)phosphonate (1.2 eq, from example 18, step 4). The reaction was stirred at room temperature for 2 hours. The crude mixture was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-5% MeOH/DCM to give the title product as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09365506B2 |
| Source dataset | uspto-grants-2016_06 |
| ORD ID | ord-233ce406dd2b475caae64ef53a1bcfec |
| Source note | uspto-grants-2016_06 |