HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methyl iodide → 4-[(R)-3-tetradecanoyloxytetradecanoylamino]-1-butanol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | Tetrabutylammonium Fluoride | HCID 2724141 | — |
| Reactant | 4-[[(1,1-Dimethylethyl)diphenylsilyl]oxy]-1-butanamine | HCID 10042117 | — |
| Reactant | (R)-3-tetradecanoyloxytetradecanoic acid | HCID 11048724 | — |
| Solvent | 1,2-Dichloroethane | HCID 11 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 4-[(R)-3-tetradecanoyloxytetradecanoylamino]-1-butanol | HCID 54331966 | 81% |
Reaction Steps
In the same manner as described in Example 20-(1), 4-amino-1-(t-butyldiphenylsilyloxy)butane (500 mg, 1.53 mmol) was acylated with (R)-3-tetradecanoyloxytetradecanoic acid (695 mg, 1.53 mmol) in the presence of EDC.MeI (595 mg, 2.0 mmol) and then deprotected with TBAF (1.0 M in THF, 2.5 mL, 2.5 mmol) in THF (15 mL) to afford 651 mg (81%) of 4-[(R)-3-tetradecanoyloxytetradecanoylamino]-1-butanol 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-6036b1038d8943a5b165b2bc21841127 |
| Source note | uspto-grants-2002_03 |