Trifluoromethanesulfonyl chloride → (5R)-3-(4-(1-Trifluoromethylsulfonyl-1,2,5,6-tetrahydropyridin-4-yl)-3-fluorophenyl)-5-(1,2,3-triazol-1-ylmethyl)oxazolidin-2-one

HRID 723802Notes

Reaction equation

HRID 723802 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.[F:27][C:28]([F:34])([F:33])[S:29](Cl)(=[O:31])=[O:30]>>[F:27][C:28]([F:34])([F:33])[S:29]([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:31])=[O:30]

Participants

3

Reactant 2

HCID 79000Trifluoromethanesulfonyl 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 69364287(5R)-3-(4-(1-Trifluoromethylsulfonyl-1,2,5,6-tetrahydropyridin-4-yl)-3-fluorophenyl)-5-(1,2,3-triazol-1-ylmethyl)oxazolidin-2-one

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 treated with trifluoromethanesulfonyl chloride essentially as in Example 76. Crude material was purified by chromatography on a 5 g silica Mega Bond Elut® column, eluting with a gradient increasing in polarity from 0 to 10% methanol in dichloromethane. Relevant fractions were combined and evaporated to give the desired product (444 mg). MS (ESP): 476 (MH+) for C18H17F4N5O4S

Workup

  1. customCrude material was purified by chromatography on a 5 g silica Mega Bond Elut® column
  2. washeluting with
  3. temperaturea gradient increasing in polarity from 0 to 10% methanol in dichloromethane
  4. customevaporated

Sources & evidence

ORD record
ord-9fff0d2ab38c475589bcf77c2b943a56
Source dataset
uspto-grants-2006_11
Patent number
US07141583B2

Reaction notes

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