Thionyl Chloride → HCID 10310255, compound

HRID 1268988Notes

Reaction equation

HRID 1268988 reaction equation
[O:1]=[S:2]1(=[O:31])[CH2:7][CH:6]=[C:5]([C:8]2[C:13]([F:14])=[CH:12][C:11]([N:15]3[CH2:19][C@H:18]([CH2:20][N:21]4[CH:25]=[C:24]([CH2:26][CH2:27]O)[N:23]=[N:22]4)[O:17][C:16]3=[O:29])=[CH:10][C:9]=2[F:30])[CH2:4][CH2:3]1.S(Cl)(Cl)=O.N12CCCN=C1CCCCC2>C(Cl)(Cl)Cl>[O:31]=[S:2]1(=[O:1])[CH2:3][CH:4]=[C:5]([C:8]2[C:13]([F:14])=[CH:12][C:11]([N:15]3[CH2:19][C@H:18]([CH2:20][N:21]4[CH:25]=[C:24]([CH:26]=[CH2:27])[N:23]=[N:22]4)[O:17][C:16]3=[O:29])=[CH:10][C:9]=2[F:30])[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 10217041HCID 10217041, compound

Product 1

HCID 10310255HCID 10310255, compoundYield 73.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

(5R)-3-[4-(1,1-Dioxo-3,6-dihydro-2H-thiopyran-4-yl)-3,5-difluorophenyl]-5-[4-(2-hydroxyethyl)-1,2,3-triazol-1-ylmethyl]oxazolidin-2-one (Example 51) (142 mg, 0.31 mmol) was suspended in dry chloroform (15 ml), thionylchloride (37 mg, 0.93 mmol) was added and the resulting mixture was refluxed for 12 hours. The solvent and eccess of thionylchloride was removed under vacuum and the residue was dissolved in acetonitrile (15 ml), 1,8-diazabicyclo[5.4.0]undec-7-ene (71 mg, 0.47 mmol) was added and the resulting mixture was refluxed for 12 hours. The solvent was removed under vacuum and the residure was purified by flash chromatography on silica gel with 1.5% methanol in dichloromethane to give the title product (100 mg).

Workup

  1. temperaturethe resulting mixture was refluxed for 12 hours
  2. customThe solvent and eccess of thionylchloride was removed under vacuum
  3. dissolutionthe residue was dissolved in acetonitrile (15 ml)
  4. temperaturethe resulting mixture was refluxed for 12 hours
  5. customThe solvent was removed under vacuum
  6. customthe residure was purified by flash chromatography on silica gel with 1.5% methanol in dichloromethane

Sources & evidence

ORD record
ord-2e991ebd0ef848deb6201ad792389fee
Source dataset
uspto-grants-2007_04
Patent number
US07199143B2

Reaction notes

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