Methanesulfonyl chloride → HCID 21084093, compound

HRID 347914Notes

Reaction equation

HRID 347914 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[O:11]=[C:12]1[N:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:16]2[S:24][C:25]([NH:33][C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[C:26]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:15]=2[CH:14]=[CH:13]1.[CH3:41][S:42](Cl)(=[O:44])=[O:43].C([O-])(O)=O.[Na+]>C1COCC1>[CH3:41][S:42]([N:33]([C:25]1[S:24][C:16]2[N:17]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:12](=[O:11])[CH:13]=[CH:14][C:15]=2[C:26]=1[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:34](=[O:40])[O:35][C:36]([CH3:37])([CH3:39])[CH3:38])(=[O:44])=[O:43]

Participants

6

Reactant 4

HCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 2724254Sodium bis(trimethylsilyl)amideHCID 21084092HCID 21084092, compound

Product 1

HCID 21084093HCID 21084093, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium bis(trimethylsilyl) amide (0.25 mL of a 1M solution in THF, 0.25 mmol) was added to a solution of the compound of Example 80 (105 mg, 0.25 mmol) in dry THF (5 mL) under a nitrogen atmosphere at 0°. After 30 min methane sulfonyl chloride (28.6 mg, 0.25 mmol) was added. The reaction mixture was allowed to warm to r.t. over 1 h then poured into saturated NaHCO3(aq) (20 mL) and the product extracted with DCM (2×20 mL). The combined organic fractions were dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by radial chromatography on silica (EtOAc) to give the title compound (115 mg, 92%). δH (CDCl3) 7.6–7.28 (11H, m), 6.55 (1H, d, J 9 Hz), 2.68 (3H, s), 1.32 (9H, s). m/z (ES+) 497 (M+H)+.

Workup

  1. extractionthe product extracted with DCM (2×20 mL)
  2. dry with materialThe combined organic fractions were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by radial chromatography on silica (EtOAc)

Sources & evidence

ORD record
ord-3dbbb795c8bf42ceb2a35d83f05fed60
Source dataset
uspto-grants-2007_02
Patent number
US07176215B2

Reaction notes

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