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

HRID 277595Notes

Reaction equation

HRID 277595 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][O:5][Si](C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[C:23]([O:38][C@H:39]([CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])[CH2:40][C:41]([OH:43])=O)(=[O:37])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36].CI.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.C(Cl)CCl>[C:23]([O:38][C@H:39]([CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])[CH2:40][C:41]([NH:1][CH2:2][CH2:3][CH2:4][OH:5])=[O:43])(=[O:37])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 2724141Tetrabutylammonium FluorideHCID 11048724(R)-3-tetradecanoyloxytetradecanoic acidHCID 151746533-Amino-1-(t-butyldiphenylsilyloxy)propane

Product 1

HCID 541644643-[(R)-3-tetradecanoyloxytetradecanoylamino]-1-propanolYield 91%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

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.

Sources & evidence

ORD record
ord-075672f3003244bb9ba71eb7cadf873c
Source dataset
uspto-grants-2002_03
Patent number
US06355257B1

Reaction notes

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