Trimethylsilyl triflate → HCID 86645808, compound

HRID 1695173Notes

Reaction equation

C([O:5][C:6](=[O:22])[C@H:7]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C@H:8]([O:15][CH3:16])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])(C)(C)C.O([Si](C)(C)C)S(C(F)(F)F)(=O)=O.C(=O)(O)[O-].[Na+]>ClCCl>[CH3:16][O:15][C@H:8]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[C@@H:7]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:6]([OH:22])=[O:5]

Participants

Conditions

Temperature: 0 °C

Procedure

The (2R,3R)-3-methoxy-2-pentylnonanoic acid t-butyl ester (450 mg, 1.43 mmol) obtained in Production Example C-9 was dissolved in anhydrous dichloromethane (10 ml), then cooled to 0° C. While the obtained solution was stirred, trimethylsilyl triflate (162 mg, 729 μmol) was added dropwise thereto. After a five-minute stirring, the solution was cooled to room temperature. After the reaction of 30 minutes, an aqueous saturated sodium bicarbonate solution was added thereto to be washed. The resulting organic layer was dried with anhydrous magnesium sulfate, filtered, and condensed. The obtained residue was purified by column chromatography (silica gel: 15 g, n-hexane/ethyl acetate=3/1) to produce the target compound (341 mg, 92%).

Workup

temperatureAfter a five-minute stirring, the solution was cooled to room temperature
customAfter the reaction of 30 minutes
washto be washed
dry with materialThe resulting organic layer was dried with anhydrous magnesium sulfate
filtrationfiltered
customcondensed
customThe obtained residue was purified by column chromatography (silica gel: 15 g, n-hexane/ethyl acetate=3/1)

Sources & evidence

ORD record: ord-dad2d65967374ef89a9b8245240c022d
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163713B2

Reaction notes

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