HuagongsheHuagongshe Chemistry Print Report · For research reference only
N-Methylbenzeneethanamine → HCID 57447918, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | N-Methylbenzeneethanamine | HCID 11503 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| 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 | HCID 69072340 | HCID 69072340 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 57447918 | HCID 57447918 | 81.4% |
Reaction Steps
N-methylphenethylamine (20 μL, 0.14 mmoL), HATU (55 mg, 0.15 mmoL) and iPr2EtN (46 μL, 0.26 mmoL) was added to a solution of 3-{5-tert-butoxy-4-({6-[(tert-butoxycarbonyl) amino]pyridin-3-yl}methyl)-3-[(4-methoxybenzyl)thio]-5-oxopentyl}benzoic acid (84 mg, 0.132 mmol) in DMF (2 mL) under argon at 0° C. The reaction mixture was stirred for 2 h and was then quenched with ice. Diethylether and water was added and the aqueous phase was extracted diethyl ether. The combined organic phase was dried and concentrated. Flash chromatography (heptan/EtOAc, 3:1) gave tert-butyl 2-({6-[(tert-butoxycarbonyl)amino]pyridin-3-yl}methyl)-3-[(4-methoxybenzyl)thio]-5-(3-{[methyl(2-phenylethyl)amino]carbonyl}phenyl)pentanoate (81 mg, 81.4%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07572817B2 |
| Source dataset | uspto-grants-2009_08 |
| ORD ID | ord-7279c547db114b48986da5cca5a4d0e1 |
| Source note | uspto-grants-2009_08 |