Tetrahydrofuran → 2-[(R)-3-decanoyloxytetradecanoylamino]ethanol

HRID 1884784Notes

Reaction equation

[C:1]([O:12][C@H:13]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:14][C:15]([OH:17])=O)(=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].C(Cl)CCl.CI.CC[CH2:37][CH2:38][N+:39](CCCC)(CCCC)CCCC.[F-].C1C[O:56]CC1>>[C:1]([O:12][C@H:13]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:14][C:15]([NH:39][CH2:38][CH2:37][OH:56])=[O:17])(=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

Reactant 4

HCID 8028Tetrahydrofuran

HCID 2724141Tetrabutylammonium Fluoride

HCID 10810916(R)-3-decanoyloxytetradecanoic acid

HCID 86585083Edc-methiodide

Product 1

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

Procedure

In the same manner as described in Example 20-(1), 2-amino-1-(t-butyldiphenylsilyloy)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-cdfaf18eb567404aa5d3610e715f4c1e
Source dataset: uspto-grants-2004_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06764840B2

Reaction notes

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