Water → HCID 52916241, compound

HRID 1752952Notes

Reaction equation

HRID 1752952 reaction equation
[CH3:1][N:2]1[N:6]=[N:5][C:4]([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[CH:18]=[CH:17][C:16]([N:19]4[CH2:23][C@H:22]([CH2:24][OH:25])[O:21][C:20]4=[O:26])=[CH:15][C:14]=3[F:27])=[CH:9][N:8]=2)=[N:3]1.[CH3:28][S:29](Cl)(=[O:31])=[O:30].C(N(CC)CC)C.O>C(Cl)Cl.[Cl-].[Na+].O>[CH3:1][N:2]1[N:6]=[N:5][C:4]([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[CH:18]=[CH:17][C:16]([N:19]4[CH2:23][C@H:22]([CH2:24][O:25][S:29]([CH3:28])(=[O:31])=[O:30])[O:21][C:20]4=[O:26])=[CH:15][C:14]=3[F:27])=[CH:9][N:8]=2)=[N:3]1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11234049Tedizolid2×

Product 1

HCID 52916241HCID 52916241, compoundYield 82.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

In 14 ml of methylenechloride was dissolved 1 g of (R)-3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-5-hydroxymethyl oxazolidin-2-on (compound 10). The solution was added with 0.46 g of methansulfonylchloride 0.46 g and 0.75 ml of triethylamine at room temperature and stirred at the same temperature for 30 minutes. Water and brine were added to the reaction mixture for washing, followed by extraction. The organic layer was dehydrated, filtrated and concentrated in vacuo thereby to provide (R)-3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-5-methansulfonyloxymethyl oxazolidin-2-on 1 g. Yield 82%.

Workup

  1. washfor washing
  2. extractionfollowed by extraction
  3. filtrationfiltrated
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-51932d3191f5405e9e51bc737ad2e344
Source dataset
uspto-grants-2015_10
Patent number
US09163043B2

Reaction notes

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