tert-Butyldimethylsilyl trifluoromethanesulphonate → HCID 67270665, compound

HRID 1697231Notes

Reaction equation

[F:1][C@@H:2]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C@H:3]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:4]([OH:7])[CH2:5][OH:6].O([Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])S(C(F)(F)F)(=O)=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Si:30]([O:7][CH:4]([CH2:5][O:6][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[CH:3]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[C@H:2]([F:1])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31]

Participants

Conditions

Temperature: 0 °C

Procedure

To a 500 mL RBF containing tert-butyl (1S,2R)-1-fluoro-3,4-dihydroxy-1-phenylbutan-2-ylcarbamate (98.00 mg, 327 μmol) was added DCM (5 mL) and the mixture was allowed to stir at 0° C. for 5 min. At this time, TEA (274 μl, 1964 μmol) and tert-butyldimethylsilyl triflate (188 μl, 818 μmol) was added to the mixture via syringe. The reaction was allowed to stir for 30 min and then queched with sodium bicarbonate (50 ml, sat). The aq. layer was extracted with DCM (3×25 ml). The combined organics were washed with brine, dried with sodium sulfate and passed through a plug of silica gel and concentrated to give 203 mg of a yellow oil that was taken directly to the next step.

Workup

stirringto stir for 30 min
extractionThe aq. layer was extracted with DCM (3×25 ml)
washThe combined organics were washed with brine
dry with materialdried with sodium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-cb4a1812d9564f18b5bf097cd5e0c2e9
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163909B2

Reaction notes

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