HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methyl iodide → 6-[(R)-3-tetradecanoyloxytetradecanoylamino]-1-hexanol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | Tetrabutylammonium Fluoride | HCID 2724141 | — |
| Reactant | (R)-3-tetradecanoyloxytetradecanoic acid | HCID 11048724 | — |
| Reactant | 6-Amino-1-(t-butyldiphenylsilyloxy)hexane | HCID 13009541 | — |
| Solvent | 1,2-Dichloroethane | HCID 11 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 6-[(R)-3-tetradecanoyloxytetradecanoylamino]-1-hexanol | HCID 53976434 | 30.5% |
Reaction Steps
In the same manner as described in Example 20-(1), 6-amino-1-(t-butyldiphenylsilyloxy)hexane (1.48 g, 4.15 mmol) was acylated with (R)-3-tetradecanoyloxytetradecanoic acid (2.07 g, 4.56 mmol) in the presence of EDC.MeI (1.35 g, 4.56 mmol) and then deprotected with TBAF (1.0 M in THF, 1.53 mL, 1.53 mmol) in THF (46 mL) to afford 700 mg (30%) of 6-[(R)-3-tetradecanoyloxytetradecanoylamino]-1-hexanol as an off-white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06355257B1 |
| Source dataset | uspto-grants-2002_03 |
| ORD ID | ord-b4c46b2b65b74b5fb6b4e988dda999bd |
| Source note | uspto-grants-2002_03 |