HuagongsheHuagongshe Chemistry Print Report · For research reference only
Benzyl Bromide → HCID 10282284, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Benzyl Bromide | HCID 7498 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 2-Naphthylalanine | HCID 185915 | — |
| Reactant | N-((3S,7R,8R,9S)-7-benzyl-8-hydroxy-9-methyl-2,6-dioxo-1,5-dioxonan-3-yl)-3-hydroxy-4-methoxypicolinamide | HCID 11236123 | — |
| Solvent | Acetone | HCID 180 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 10282284 | HCID 10282284 | 39% |
Reaction Steps
Benzyl bromide (23.5 mL) was added to a solution of Nal (11.3 mol, 1.68 g) in acetone (60 mL). Compound 1 (22.5 mmol, 10 g) was added followed by powdered K2CO3.(38.8 mol, 5.3 g) and the mixture stirred vigorously overnight. The mixture was diluted with EtOAc (150 mL) and washed with H2O (2×150 mL). The organic layer was dried (MgSO4), and concentrated in vacuo. Purification via column chromatography (acetone/hexanes) gave 4.70 g (39%) of Compound 2 as an off-white solid. 1H-NMR and MS (M+1)+=535 were consistent for Compound 2.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06903219B2 |
| Source dataset | uspto-grants-2005_06 |
| ORD ID | ord-9b50d8346d7e4d33857678b75d69e0ae |
| Source note | uspto-grants-2005_06 |