HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methyl iodide → 3-[(R)-3-tetradecanoyloxytetradecanoylamino]-1-propanol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | Tetrabutylammonium Fluoride | HCID 2724141 | — |
| Reactant | (R)-3-tetradecanoyloxytetradecanoic acid | HCID 11048724 | — |
| Reactant | 3-Amino-1-(t-butyldiphenylsilyloxy)propane | HCID 15174653 | — |
| Solvent | 1,2-Dichloroethane | HCID 11 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 3-[(R)-3-tetradecanoyloxytetradecanoylamino]-1-propanol | HCID 54164464 | 91% |
Reaction Steps
In the same manner as described in Example 20-(1), 3-amino-1-(t-butyldiphenylsilyloxy)propane (470 mg, 1.5 mmol) was acylated with (R)-3-tetradecanoyloxytetradecanoic acid (680 mg, 1.5 mmol) in the presence of EDC.MeI (595 mg, 2.0 mmol) and then deprotected with TBAF (1.0 M in THF, 2.0 mL, 2.0 mmol) in THF (10 mL) to afford 698 mg (91%) of 3-[(R)-3-tetradecanoyloxytetradecanoylamino]-1-propanol as an off-white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06113918 |
| Source dataset | uspto-grants-2000_09 |
| ORD ID | ord-d71deddb6ec342a49daa0804e816ea0d |
| Source note | uspto-grants-2000_09 |