Methyl iodide → 4-[(R)-3-tetradecanoyloxytetradecanoylamino]-1-butanol

HRID 277596Notes

Reaction equation

HRID 277596 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][Si](C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[C:24]([O:39][C@H:40]([CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])[CH2:41][C:42]([OH:44])=O)(=[O:38])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37].CI.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.C(Cl)CCl>[C:24]([O:39][C@H:40]([CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])[CH2:41][C:42]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][OH:6])=[O:44])(=[O:38])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 2724141Tetrabutylammonium FluorideHCID 100421174-[[(1,1-Dimethylethyl)diphenylsilyl]oxy]-1-butanamineHCID 11048724(R)-3-tetradecanoyloxytetradecanoic acid

Product 1

HCID 543319664-[(R)-3-tetradecanoyloxytetradecanoylamino]-1-butanolYield 81%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

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.

Sources & evidence

ORD record
ord-6036b1038d8943a5b165b2bc21841127
Source dataset
uspto-grants-2002_03
Patent number
US06355257B1

Reaction notes

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