Methanesulfonyl chloride → (5R)-3-(4-(1-Methylsulfonyl-1,2,5,6-tetrahydropyridin-4-yl)-3-fluoro-phenyl)-5-(1,2,3-triazol-1-ylmethyl)oxazolidin-2-one

HRID 723800Notes

Reaction equation

HRID 723800 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][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]=[CH:23][N:22]=[N:21]4)[O:16][C:15]3=[O:25])=[CH:10][C:9]=2[F:26])=[CH:4][CH2:3]1.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>ClCCl.CN(C)C1C=CN=CC=1>[CH3:27][S:28]([N:2]1[CH2:7][CH2:6][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]=[CH:23][N:22]=[N:21]4)[O:16][C:15]3=[O:25])=[CH:10][C:9]=2[F:26])=[CH:4][CH2:3]1)(=[O:30])=[O:29]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 69364214(5R)-3-(4-(1,2,5,6-Tetrahydropyridin-4-yl)-3-fluorophenyl)-5-(1,2,3-triazol-1-ylmethyl)-oxazolidin-2-one hydrochloride

Product 1

HCID 69363627(5R)-3-(4-(1-Methylsulfonyl-1,2,5,6-tetrahydropyridin-4-yl)-3-fluoro-phenyl)-5-(1,2,3-triazol-1-ylmethyl)oxazolidin-2-oneYield 7.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(5R)-3-(4-(1,2,5,6-Tetrahydropyridin-4-yl)-3-fluorophenyl)-5-(1,2,3-triazol-1-ylmethyl)-oxazolidin-2-one hydrochloride (380 mg, 1 mM) was suspended in dichloromethane (15 ml), 4-dimethylaminopyridine (305 mg, 2.5 mM) added, and the mixture stirred vigorously for 15 minutes. After cooling to 0° C. under nitrogen, methanesulfonyl chloride (229 mg, 2 mM) was added dropwise, and the mixture stirred 18 hours at ambient temperature. Precipitated solid was removed, and the organic solution concentrated, then purified by chromatography on a 10 g silica Mega Bond Elut® column, eluting with a gradient increasing in polarity from 0 to 5% methanol in dichloromethane. Relevant fractions were combined and evaporated to give the desired product (30 mg). MS (ESP): 422 (MH+) for C18H20FN5O4S

Workup

  1. stirringthe mixture stirred 18 hours at ambient temperature
  2. customPrecipitated solid
  3. customwas removed
  4. concentrationthe organic solution concentrated
  5. custompurified by chromatography on a 10 g silica Mega Bond Elut® column
  6. washeluting with
  7. temperaturea gradient increasing in polarity from 0 to 5% methanol in dichloromethane
  8. customevaporated

Sources & evidence

ORD record
ord-c0279c070d794c9f97ddc0ad0c278ce4
Source dataset
uspto-grants-2006_11
Patent number
US07141583B2

Reaction notes

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