HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → (S)-tert-butyl 3-(2,5,8,11,14,17,20-heptaoxadocosan-22-yl(methyl)carbamoyl)piperidine-1-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | (3S)-1-((tert-butoxy)carbonyl)piperidine-3-carboxylic acid | HCID 6951168 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | mPEG7-NHMe | HCID 86705991 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | (S)-tert-butyl 3-(2,5,8,11,14,17,20-heptaoxadocosan-22-yl(methyl)carbamoyl)piperidine-1-carboxylate | HCID 66587538 | 212.5% |
Reaction Steps
To a solution of Boc-(S)-nipecotic acid (137 mg, 0.60 mmol), N-methyl-2,5,8,11,14,17,20-heptaoxadocosan-22-amine 135c.1 (310 mg, 0.88 mmol) and DIPEA (335 mg, 2.6 mmol) in DMF (3 mL) was added HATU (285 mg, 0.75 mmol). The reaction was stirred for 1 hour and then the DMF was removed under vacuum. The residue was added to saturated aqueous NaHCO3 (10 mL) and extracted with DCM (3×20 mL). The combined organic layers were dried (Na2SO4) and concentrated to give (S)-tert-butyl 3-(2,5,8,11,14,17,20-heptaoxadocosan-22-yl(methyl)carbamoyl)piperidine-1-carboxylate (720 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09301951B2 |
| Source dataset | uspto-grants-2016_04 |
| ORD ID | ord-3997f2f6d79c482f998f20058553e57e |
| Source note | uspto-grants-2016_04 |