Methyl iodide → 2-[(R)-3-decanoyloxytetradecanoylamino]ethanol

HRID 1830452Notes

Reaction equation

HRID 1830452 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][Si](C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[C:22]([O:33][C@H:34]([CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[CH2:35][C:36]([OH:38])=O)(=[O:32])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31].CI.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.C(Cl)CCl>[C:22]([O:33][C@H:34]([CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[CH2:35][C:36]([NH:1][CH2:2][CH2:3][OH:4])=[O:38])(=[O:32])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 2724141Tetrabutylammonium FluorideHCID 10810916(R)-3-decanoyloxytetradecanoic acidHCID 110010432-(t-Butyldiphenylsilyloxy)ethylamine

Product 1

HCID 537397632-[(R)-3-decanoyloxytetradecanoylamino]ethanolYield 81%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

In the same manner as described in Example 20-(1), 2-amino-1-(t-butyldiphenylsilyloxy)ethane (450 mg, 1.5 mmol) was acylated with (R)-3-decanoyloxytetradecanoic acid (600 mg, 1.5 mmol) in the presence of EDC.MeI (594 mg, 2.0 mmol) and then deprotected with TBAF (1.0 M in THF, 2.5 mL, 2.5 mmol) in THF (10 mL) to afford 488 mg (81%) of 2-[(R)-3-decanoyloxytetradecanoylamino]ethanol as an off-white solid.

Sources & evidence

ORD record
ord-528e7b1139a340059800fa8b903c4b0f
Source dataset
uspto-grants-2006_06
Patent number
US07063967B2

Reaction notes

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