Methanesulfonyl chloride → HCID 69364653, compound

HRID 723767Notes

Reaction equation

HRID 723767 reaction equation
Cl.[NH2:2][C@H:3]1[CH2:7][CH2:6][N: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])[CH2:4]1.C(=O)(O)[O-].[Na+].[CH3:32][S:33](Cl)(=[O:35])=[O:34]>ClCCl>[CH3:32][S:33]([NH:2][C@H:3]1[CH2:7][CH2:6][N: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])[CH2:4]1)(=[O:35])=[O:34]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 69363410HCID 69363410, compound

Product 1

HCID 69364653HCID 69364653, compoundYield 10.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(5R)-3-(4-((3S)-3-Aminopyrrolidin-1-yl)-3-fluorophenyl)-5-(1,2,3-triazol-1-ylmethyl)-oxazolidin-2-one hydrochloride (250 mg, 0.65 mM), in dichloromethane (20 ml) was cooled to 0° and treated with 5% sodium bicarbonate solution (10 ml). The resulting suspension was stirred vigorously, methanesulfonyl chloride (290 mg, 2.5 mM) added, and stirring continued for 18 hours at ambient temperature. Dichloromethane (10 ml) was added, the organic layer separated, and diluted with isohexane (30 ml). The precipitate was filtered, triturated with 2% sodium dihydrogen phosphate, and purified by chromatography on a 2 g silica Mega Bond Elut® column, eluting with a gradient increasing in polarity from 0 to 8% methanol in dichloromethane. Relevant fractions were combined and evaporated to give the desired product (28 mg).

Workup

  1. stirringstirring
  2. customthe organic layer separated
  3. additiondiluted with isohexane (30 ml)
  4. filtrationThe precipitate was filtered
  5. customtriturated with 2% sodium dihydrogen phosphate
  6. custompurified by chromatography on a 2 g silica Mega Bond Elut® column
  7. washeluting with a gradient
  8. temperatureincreasing in polarity from 0 to 8% methanol in dichloromethane
  9. customevaporated

Sources & evidence

ORD record
ord-b8a627f3d60e4e6a930b3187781ef717
Source dataset
uspto-grants-2006_11
Patent number
US07141583B2

Reaction notes

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