Water → (5R)-3-[4-(3,6-Dihydro-1,1-dioxido-2H-thiopyran-4-yl)-3-fluorophenyl]-5-[(4-ethoxy-1H-1,2,3-triazol-1-yl)methyl]-2-oxazolidinone

HRID 1268979Notes

Reaction equation

HRID 1268979 reaction equation
[O:1]=[S:2]1(=[O:25])[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]=[N+:21]=[N-:22])[O:16][C:15]3=[O:23])=[CH:10][C:9]=2[F:24])[CH2:4][CH2:3]1.[CH2:26]([O:28][C:29]#[CH:30])[CH3:27].N1C(C)=CC=CC=1C.O>C(#N)C.[Cu](I)I>[O:25]=[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:27]=[C:26]([O:28][CH2:29][CH3:30])[N:22]=[N:21]4)[O:16][C:15]3=[O:23])=[CH:10][C:9]=2[F:24])[CH2:6][CH2:7]1

Participants

7

Reactant 4

HCID 962WaterHCID 79372,6-LutidineHCID 61239Ether, ethyl ethynylHCID 11222326HCID 11222326, compound

Product 1

HCID 10127293(5R)-3-[4-(3,6-Dihydro-1,1-dioxido-2H-thiopyran-4-yl)-3-fluorophenyl]-5-[(4-ethoxy-1H-1,2,3-triazol-1-yl)methyl]-2-oxazolidinoneYield 76.3%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 6342AcetonitrileSolvent

Procedure

(5R)-3-[4-(1,1-Dioxo-3,6-dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-5-(azidomethyl)oxazolidin-2-one (Reference Example 2) (733 mg, 2.0 mmol) was dissolved in dry acetonitrile (8 ml). Ethoxyacetylene (420 mg, 6.0 mmol), 2,6-lutidine (236 mg, 2.2 mmol) and copper iodide (38 mg, 10 mmol %) were added and the resulting mixture was stirred at room temperature for 12 hours. Water was added and the mixture was extracted with dichloromethane (3×100 ml). The combined organic layers were concentrated under vacuum and the residue was purified by flash chromatography on silica gel with 5% of methanol in dichloromethane to give the title product (666 mg).

Workup

  1. extractionthe mixture was extracted with dichloromethane (3×100 ml)
  2. concentrationThe combined organic layers were concentrated under vacuum
  3. customthe residue was purified by flash chromatography on silica gel with 5% of methanol in dichloromethane

Sources & evidence

ORD record
ord-6cfdda7f3b6c46009e80bd628e737eb2
Source dataset
uspto-grants-2007_04
Patent number
US07199143B2

Reaction notes

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