Methyl iodide → 6-[(R)-3-tetradecanoyloxytetradecanoylamino]-1-hexanol
Reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][Si](C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[C:26]([O:41][C@H:42]([CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57])[CH2:43][C:44](O)=[O:45])(=[O:40])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39].CI.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.C(Cl)CCl>[C:26]([O:41][C@H:42]([CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57])[CH2:43][C:44]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8])=[O:45])(=[O:40])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
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.
Sources & evidence
- ORD record
- ord-b4c46b2b65b74b5fb6b4e988dda999bd
- Source dataset
- uspto-grants-2002_03
- Patent number
- US06355257B1
Reaction notes
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