HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diethylamine → HCID 67107644, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diethylamine | HCID 8021 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 1-[(Tert-butoxy)carbonyl]azetidine-2-carboxylic acid | HCID 3623886 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 67107644 | HCID 67107644 | 64.6% |
Reaction Steps
A solution of diethylamine (0.453 g), azetidine-1,2-dicarboxylic acid-1-t-butyl ester (Intermediate 209, 0.891 g), HATU (2.53 g) and DIPEA (1.72 g) in acetonitrile (20 ml) was stirred at room temperature under argon for 4 hours. The mixture was evaporated to dryness and ethyl acetate was added to the residue. The solution was washed with 1M NaOH, brine and water then dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of methanol and DCM with a gradient of 0-4% to give t-butyl 2-diethylcarbamoylazetidine-1-carboxylate (0.733 g) as light brown oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09067905B2 |
| Source dataset | uspto-grants-2015_06 |
| ORD ID | ord-25d2f1df4aea4b0d9e0d888e96e96f74 |
| Source note | uspto-grants-2015_06 |