Triethylamine → HCID 10128237, compound

HRID 1268974Notes

Reaction equation

HRID 1268974 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.C(OP([O-])OCC)C.C(N(CC)CC)C>C(O)C.ClCCl>[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](/[CH:25]=[CH: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

6

Reactant 3

HCID 8471TriethylamineHCID 3780918DiethylphosphiteHCID 10175195HCID 10175195, compound

Product 1

HCID 10128237HCID 10128237, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °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 (0.4 g, 0.69 mmol) was dissolved/supended in ethanol (2 ml) and diethylphosphite (0.36 ml, 2.79 mmol). Triethylamine (0.195 ml, 1.39 mmol) was added and the reaction mixture heated under vigorous stirring at 90° C. for 5 hours. It was cooled to room temperature, diluted with dichloromethane, washed with phosphate buffer (pH 7) and dried over sodium sulfate. Chromatography on silica gel with dichloromethane/DMF (50:1 to 40:1) gave 151 mg (44%) of the title compound as a colourless solid.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureIt was cooled to room temperature
  3. washwashed with phosphate buffer (pH 7)
  4. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-edb379f727794d8fa54c9f0258c4d3e1
Source dataset
uspto-grants-2007_04
Patent number
US07199143B2

Reaction notes

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