HuagongsheHuagongshe Chemistry Print Report · For research reference only
Benzoic Acid → (E)-tert-butyl 2-(6-benzamidohex-3-enamido)phenylcarbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Benzoic Acid | HCID 243 | — |
| 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 60207723 | HCID 60207723 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | (E)-tert-butyl 2-(6-benzamidohex-3-enamido)phenylcarbamate | HCID 60207724 | 65.4% |
Reaction Steps
A mixture of (E)-tert-butyl 2-(6-aminohex-3-enamido)phenylcarbamate (100 mg, 0.3134 mmol), HATU (119.1 mg, 0.3134 mmol), DIEA (0.25 ml), benzoic acid (38 mg, 03134 mmol) in DCM was stirred at RT for 5 hours, The reaction mixture was poured onto 50 mL of ethyl acetate and 20 mL of water. The organic layers were washed with water (20 mL×3) and brine (3×20 mL), dried over Na2SO4 and concentrated to give the desired compound of (E)-tert-butyl 2-(6-benzamidohex-3-enamido)phenylcarbamate (86.16 mg, yield 65%) as a white solid after purification by column chromatography on silica gel (eluent: DCM:MeOH=200:1). LC-MS found 424 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09265734B2 |
| Source dataset | uspto-grants-2016_02 |
| ORD ID | ord-6fbd0d01aef24e2db58cc5e87d905868 |
| Source note | uspto-grants-2016_02 |