Methanesulfonyl chloride → Trifluoromethanesulfonic acid 6-methanesulfonyloxy-1-[4-(2-piperidin-1-yl-ethoxy)-benzoyl]-naphthalen-2-yl ester

HRID 916872Notes

Reaction equation

HRID 916872 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([C:12](=[O:28])[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][N:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)=[CH:15][CH:14]=1)=[C:7]([O:29][S:30]([C:33]([F:36])([F:35])[F:34])(=[O:32])=[O:31])[CH:6]=[CH:5]2.C(N(C(C)C)CC)(C)C.[CH3:46][S:47](Cl)(=[O:49])=[O:48].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:46][S:47]([O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([C:12](=[O:28])[C:13]1[CH:14]=[CH:15][C:16]([O:19][CH2:20][CH2:21][N:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)=[CH:17][CH:18]=1)=[C:7]([O:29][S:30]([C:33]([F:35])([F:36])[F:34])(=[O:32])=[O:31])[CH:6]=[CH:5]2)(=[O:49])=[O:48]

Participants

6

Reactant 4

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 11584459Trifluoromethanesulfonic acid 6-hydroxy-1-[4-(2-piperidin-1-yl-ethoxy)-benzoyl]-naphthalen-2-yl ester

Product 1

HCID 11628623Trifluoromethanesulfonic acid 6-methanesulfonyloxy-1-[4-(2-piperidin-1-yl-ethoxy)-benzoyl]-naphthalen-2-yl esterYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Suspend trifluoro-methanesulfonic acid 6-hydroxy-1-[4-(2-piperidin-1-yl-ethoxy)-benzoyl]-naphthalen-2-yl ester (12.5 g, 24 mmol) in dry methylene chloride (100 ml). Add diisopropylethylamine (8.3 mL, 48 mmol). Slowly add methanesulfonyl chloride (2.7 mL, 36 mmol). Pour the reaction into saturated aqueous sodium bicarbonate after 20 minutes and extract with methylene chloride. Wash the organic layer with water, dry with sodium sulfate, filter and concentrate in vacuo to yield 14.2 g (99%) of the title compound as an amber foam. 1H NMR (CDCl3) δ8.05 (d, J-=9.2 Hz, 1H), 7.90 (d, J=1.9 Hz, 1H), 7.76 (d, J=8.2 Hz, 2H), 7.75 (d, J=9.0 Hz, 1H), 7.59 (d, J=9.2 Hz, 1H), 7.43 (dd, J=9.2, 1.7 Hz, 1H), 6.94 (d, J=8.2 Hz, 2H), 4.17 (t, J=5.7 Hz, 2H), 3.23 (s, 3H), 2.79 (t, J=5.2 Hz, 2H), 2.5 (bs, 4H), 1.63-1.57 (m, 4H), 1.48-1.40 (m, 2H); LCMS mass spectrum (ion spray): m/z=602.3 (M+H).

Workup

  1. additionPour
  2. extractionextract with methylene chloride
  3. washWash the organic layer with water
  4. dry with materialdry with sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-6dc0b4d314394b988b8700e78b0d27fb
Source dataset
uspto-grants-2007_09
Patent number
US07271264B2

Reaction notes

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