Methanesulfonyl chloride → Methanesulfonic acid 2'-fluoro-5'-methoxy-2-(1-methoxy-cyclopentyl)-biphenyl-4-ylmethyl ester

HRID 404386Notes

Reaction equation

HRID 404386 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][OH:17])=[CH:12][C:11]=1[C:18]1([O:23][CH3:24])[CH2:22][CH2:21][CH2:20][CH2:19]1.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][O:17][S:26]([CH3:25])(=[O:28])=[O:27])=[CH:12][C:11]=1[C:18]1([O:23][CH3:24])[CH2:19][CH2:20][CH2:21][CH2:22]1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 57706279[2'-Fluoro-5'-methoxy-2-(1-methoxy-cyclopentyl)-biphenyl-4-yl]-methanol

Product 1

HCID 58379877Methanesulfonic acid 2'-fluoro-5'-methoxy-2-(1-methoxy-cyclopentyl)-biphenyl-4-ylmethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 20.6 (30 mg, 91 mmol) in 1 mL of DCM at 0° C., was added TEA (11 mg, 109 μmol) followed by methanesulfonyl chloride (12 mg, 109 mmol). The mixture was stirred at room temperature for 30 minutes. The reaction was then quenched with water and extracted with EtOAc. The organic layers were combined, washed with water and brine and then dried over anhydrous sodium sulfate. After filtration, the organic solvent was removed in vacuo to give the product as a residue which was used without further purification. MS ESI m/e: 409.1 (M+H)+.

Workup

  1. customThe reaction was then quenched with water
  2. extractionextracted with EtOAc
  3. washwashed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. customthe organic solvent was removed in vacuo
  7. customto give the product as a residue which
  8. customwas used without further purification

Sources & evidence

ORD record
ord-a0bd8014e75649c5a29711fc5cfb1cf9
Source dataset
uspto-grants-2014_06
Patent number
US08748462B2

Reaction notes

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