Triethylamine → HCID 497408, compound

HRID 1167446Notes

Reaction equation

HRID 1167446 reaction equation
Cl.Cl.[N:3]1([C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:19][C@H:18]([CH2:20][O:21][C:22]4[CH:26]=[CH:25][O:24][N:23]=4)[O:17][C:16]3=[O:27])=[CH:11][C:10]=2[F:28])[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.C(N(CC)CC)C.[CH3:36][S:37](Cl)(=[O:39])=[O:38]>N1C=CC=CC=1.ClCCl>[CH3:36][S:37]([N:6]1[CH2:5][CH2:4][N:3]([C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:19][C@H:18]([CH2:20][O:21][C:22]4[CH:26]=[CH:25][O:24][N:23]=4)[O:17][C:16]3=[O:27])=[CH:11][C:10]=2[F:28])[CH2:8][CH2:7]1)(=[O:39])=[O:38]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 69980303HCID 69980303, compound

Product 1

HCID 497408HCID 497408, compoundYield 82.9%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

3-(4-(piperazin-1-yl)-3-fluorophenyl)-5(R)-(isoxazol-3-yloxymethyl)oxazolidin-2-one dihydrochloride (433 mg, 1 mmol) in pyridine (15 ml) and dichloromethane (15 ml) was treated with triethylarnine (353 mg, 3.5 mmol) and stirred for 30 minutes at ambient temperature. Methanesulfonyl chloride (138 mg, 1.2 mmol) was added and the mixture stirred for 18 hours. The mixture was diluted with dichloromethane (50 ml), washed with water (2×25 ml), saturated brine (25 ml), and dried (magnesium sulfate). After evaporation to dryness and azeotroping with toluene (10 ml), the residue was triturated with diethyl ether to give the desired product (365 mg).

Workup

  1. stirringthe mixture stirred for 18 hours
  2. washwashed with water (2×25 ml), saturated brine (25 ml)
  3. dry with materialdried (magnesium sulfate)
  4. customAfter evaporation to dryness
  5. customazeotroping with toluene (10 ml)
  6. customthe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-05659b3aac7b4f49a47bf21979ed0dc0
Source dataset
uspto-grants-2003_09
Patent number
US06617339B1

Reaction notes

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