Tetrabutylammonium Fluoride → HCID 59347048, compound

HRID 1039713Notes

Reaction equation

[Si]([O:8][CH2:9][C@H:10]1[O:14][C:13]([CH3:16])([CH3:15])[N:12]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C@H:11]1[CH2:24][C:25]1[N:26]=[C:27]([CH3:30])[S:28][CH:29]=1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:8][CH2:9][C@H:10]1[O:14][C:13]([CH3:16])([CH3:15])[N:12]([C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])[C@H:11]1[CH2:24][C:25]1[N:26]=[C:27]([CH3:30])[S:28][CH:29]=1

Participants

Conditions

Temperature: 0 °C

Procedure

(4S,5S)-Tert-butyl 5-((tert-butyldimethylsilyloxy)methyl)-2,2-dimethyl-4-((2-methylthiazol-4-yl)methyl)oxazolidine-3-carboxylate (0.100 g, 0.219 mmol) was dissolved in THF (4 mL) and cooled to 0° C. Next, TBAF (0.547 ml, 0.547 mmol) was added dropwise and the reaction was stirred 1 hr. and then quenched with saturated ammonium chloride and diluted with EtOAc. The layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with water, brine, dried over sodium sulfate, and concentrated. Purification by column chromatography (2.5:1 Hexanes/EtOAc) afforded the title compound.

Workup

customand then quenched with saturated ammonium chloride
additiondiluted with EtOAc
customThe layers were separated
extractionthe aqueous layer was extracted with ethyl acetate
washThe combined organic layers were washed with water, brine
dry with materialdried over sodium sulfate
concentrationconcentrated
customPurification by column chromatography (2.5:1 Hexanes/EtOAc)

Sources & evidence

ORD record: ord-0ccdb60febe445299d815b88db3ee81d
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08552181B2

Reaction notes

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