Methanesulfonyl chloride → HCID 90408426, compound

HRID 1855087Notes

Reaction equation

HRID 1855087 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[F:6][C:7]1[CH:8]=[C:9]([C:20]23[CH2:27][CH2:26][C:23]([CH2:28][CH2:29][OH:30])([CH2:24][CH2:25]2)[CH2:22][O:21]3)[CH:10]=[C:11]([O:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][O:15]2)[CH:12]=1>C(Cl)Cl>[CH3:1][S:2]([O:30][CH2:29][CH2:28][C:23]12[CH2:24][CH2:25][C:20]([C:9]3[CH:10]=[C:11]([O:13][CH:14]4[CH2:19][CH2:18][CH2:17][CH2:16][O:15]4)[CH:12]=[C:7]([F:6])[CH:8]=3)([CH2:27][CH2:26]1)[O:21][CH2:22]2)(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 90408708HCID 90408708, compound

Product 1

HCID 90408426HCID 90408426, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Methanesulfonyl chloride (0.100 mL, 1.28 mmol) was added to a solution of 2-(1-(3-fluoro-5-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)-2-oxabicyclo[2.2.2]octan-4-yl)ethanol (36G; 0.373 g, 1.06 mmol) and TEA (0.46 mL. 3.19 mmol) in DCM (5 mL) at 0° C. and the reaction was stirred at 0° C. for 2 h and then concentrated in vacuo. The residue was dissolved in EtOAc (50 mL), washed with 1 N aq. HCl and water, sat. aq. NaHCO3, and water again. The organic layer was dried (MgSO4) and filtered. The filtrate was concentrated in vacuo to give the crude title compound (0.456 g, 1.06 mmol, 100% yield) as a clear oil.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in EtOAc (50 mL)
  3. washwashed with 1 N aq. HCl and water, sat. aq. NaHCO3, and water again
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-6621e89853d04b97bfd923401703a8d5
Source dataset
uspto-grants-2015_02
Patent number
US08962660B2

Reaction notes

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