HuagongsheHuagongshe Chemistry Print Report · For research reference only
Benzylethanolamine → (R)-tert-butyl (1-(benzyl(2-hydroxyethyl)amino)-3-methyl-1-oxobutan-2-yl)carbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Benzylethanolamine | HCID 4348 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | (2R)-2-(((tert-butoxy)carbonyl)amino)-3-methylbutanoic acid | HCID 637605 | — |
| 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 | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (R)-tert-butyl (1-(benzyl(2-hydroxyethyl)amino)-3-methyl-1-oxobutan-2-yl)carbamate | HCID 58602496 | 90.8% |
Reaction Steps
To a solution of (R)-2-((tert-butoxycarbonyl)amino)-3-methylbutanoic acid (2.0 g, 9.20 mmol) in CH2Cl2 (40 mL) were added 2-(benzylamino)ethanol (1.3 g, 8.80 mmol), HATU (5.30 g, 13.8 mmol) and Et3N (2.80 g, 27.6 mmol) under N2. The mixture was stirred at rt overnight. The mixture was added water (20 mL) and extracted with EtOAc (3×30 mL). The combined organic layers were washed with brine (20 mL), dried over anhydrous Na2SO4, filtered, concentrated and then purified by column chromatography on silica gel to afford (R)-tert-butyl(1-(benzyl(2-hydroxyethyl)amino)-3-methyl-1-oxobutan-2-yl)carbamate (2.80 g, 88% yield) as a white solid. LC-MS m/z 351.2 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09006244B2 |
| Source dataset | uspto-grants-2015_04 |
| ORD ID | ord-c5eb0d8bf26d4f648836b138468a41c1 |
| Source note | uspto-grants-2015_04 |