Boron tribromide → HCID 10173091, compound

HRID 1268984Notes

Reaction equation

[O:1]=[S:2]1(=[O:30])[CH2:7][CH:6]=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][N:20]4[CH:24]=[C:23]([O:25]CC)[N:22]=[N:21]4)[O:16][C:15]3=[O:28])=[CH:10][C:9]=2[F:29])[CH2:4][CH2:3]1.B(Br)(Br)Br>ClCCl>[O:30]=[S:2]1(=[O:1])[CH2:3][CH:4]=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][N:20]4[CH:24]=[C:23]([OH:25])[N:22]=[N:21]4)[O:16][C:15]3=[O:28])=[CH:10][C:9]=2[F:29])[CH2:6][CH2:7]1

Participants

Conditions

Temperature: 0 °C

Procedure

(5R)-3-[4-(1,1-Dioxo-3,6-dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-5-[4-ethoxy-1,2,3-triazol-1-ylmethyl]oxazolidin-2-one (Example 35) (390 mg, 0.89 mmol) was dissolved in dry dichloromethane (5 ml), cooled down to 0° C., boron tribromide was added via syringe, then the mixture was warmed up to 45° C. and stirred for 48 hours. It was quenched dropwise with water (10 ml) and was extracted with dichloromethane. The combined organic layer was concentrated under vacuum and the residue was purified by reverse phase chromatography with 5%–95% acetonitrile in water (containing 0.1% TFA) to give the title product (221 mg).

Workup

temperaturethe mixture was warmed up to 45° C.
customIt was quenched dropwise with water (10 ml)
extractionwas extracted with dichloromethane
concentrationThe combined organic layer was concentrated under vacuum
customthe residue was purified by reverse phase chromatography with 5%–95% acetonitrile in water (containing 0.1% TFA)

Sources & evidence

ORD record: ord-0e86c7e8d7d246dea50c0a264535caaa
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07199143B2

Reaction notes

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