1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 10239105, compound

HRID 1268975Notes

Reaction equation

[O:1]=[S:2]1(=[O:31])[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]([CH:25]=[C:26](Br)[Br:27])[N:22]=[N:21]4)[O:16][C:15]3=[O:29])=[CH:10][C:9]=2[F:30])[CH2:4][CH2:3]1.N12CCCN=C1CCCCC2>CS(C)=O>[O:31]=[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]([C:25]#[C:26][Br:27])[N:22]=[N:21]4)[O:16][C:15]3=[O:29])=[CH:10][C:9]=2[F:30])[CH2:6][CH2:7]1

Participants

Conditions

Temperature: 15 °C

Procedure

(5R)-3-[4-(1,1-Dioxo-3,6-dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-5-[4-(2,2-dibromoethenyl)-1,2,3-triazol-1-ylmethyl]oxazolidin-2-one (Example 25) (0.5 g, 0.87 mmol) was dissolved in DMSO (87 ml) and cooled to 15° C. 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) (0.262 ml, 1.75 mmol), dissolved in DMSO (1.7 ml), was added drop wise under stirring over 30 minutes. The temperature was maintained at 15–18° C. and after 6 hours more DBU (0.125 ml, 0.83 mmol) was added drop wise via a syringe and the resulting solution stirred for another 30 minutes. The reaction was quenched with cold aqueous HCl (0.5 M), extracted with dichloromethane, washed with water and dried over sodium sulfate. Chromatography on silica gel with hexanes/acetone (1.5:1 to 1:1) gave 108 mg (25%) of the title product as a colourless solid.

Workup

additionwas added drop wise
additionwas added drop wise via a syringe
stirringthe resulting solution stirred for another 30 minutes
customThe reaction was quenched with cold aqueous HCl (0.5 M)
extractionextracted with dichloromethane
washwashed with water
dry with materialdried over sodium sulfate

Sources & evidence

ORD record: ord-e6b7d69170f74468bccc2e6951d77920
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07199143B2

Reaction notes

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