HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 3-((2S,3R)-4-azido-1-cyclohexyl-3-hydroxybutan-2-ylamino)-4-(3-((3-methoxypropoxy)(phenyl)methyl)piperidin-1-yl)cyclobut-3-ene-1,2-dione
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 3-((3-Methoxypropoxy)(phenyl)methyl)piperidine | HCID 57419600 | — |
| Reactant | 3-((2S,3R)-4-Azido-1-cyclohexyl-3-hydroxybutan-2-ylamino)-4-methoxycyclobut-3-ene-1,2-dione | HCID 57786524 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | 3-((2S,3R)-4-azido-1-cyclohexyl-3-hydroxybutan-2-ylamino)-4-(3-((3-methoxypropoxy)(phenyl)methyl)piperidin-1-yl)cyclobut-3-ene-1,2-dione | HCID 57786468 | 67.3% |
Reaction Steps
3-((2S,3R)-4-Azido-1-cyclohexyl-3-hydroxybutan-2-ylamino)-4-methoxycyclobut-3-ene-1,2-dione (35 mg, 0.11 mmol), the HCl salt of 3-((3-methoxypropoxy)(phenyl)methyl)piperidine (48 mg, 0.16 mmol), and Et3N (100 μL, 0.7 mmol) were dissolved in acetonitrile (1 mL). The reaction was allowed to stir at rt overnight. The solvent was evaporated and the product was isolated by preparative HPLC to give 3-((2S,3R)-4-azido-1-cyclohexyl-3-hydroxybutan-2-ylamino)-4-(3-((3-methoxypropoxy)(phenyl)methyl)piperidin-1-yl)cyclobut-3-ene-1,2-dione (41 mg). MS m/z 554 (M+H+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07872028B2 |
| Source dataset | uspto-grants-2011_01 |
| ORD ID | ord-e87d67c52ae944b3badee6ca2306d210 |
| Source note | uspto-grants-2011_01 |