HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → HCID 178428946, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Tri-o-tolylphosphine | HCID 80271 | — |
| Reactant | (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[2-(benzyloxy)-5-(4-bromobenzyl)-4-methylphenyl]-D-glucitol | HCID 67305342 | — |
| Reactant | HCID 178457569 | HCID 178457569 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 178428946 | HCID 178428946 | 46% |
Reaction Steps
To an acetonitrile solution (3 mL) of (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[2-(benzyloxy)-5-(4-bromobenzyl)-4-methylphenyl]-D-glucitol (271 mg, 0.305 mmol) were added dibenzyl[(Z)-(allylamino)methylylidene]biscarbamate (335 mg, 0.914 mmol), palladium(II) acetate (18 mg, 0.0791 mmol), tri-O-tolylphosphine (61 mg, 0.201 mmol) and triethylamine (154 mg, 1.52 mmol), and reacted at 120° C. for 20 minutes with microwave manufactured by Biotage. The reaction solution was evaporated under reduced pressure. Thus obtained residue was purified with silica gel column chromatography (hexane:ethyl acetate=5:1) to obtain the title compound (163 mg, 46%) as a pale yellow amorphous compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07973012B2 |
| Source dataset | uspto-grants-2011_07 |
| ORD ID | ord-c92218c3cd7241f28c0ba5bfabb53b3c |
| Source note | uspto-grants-2011_07 |