2-(Trifluoromethoxy)benzene-1-sulfonyl chloride → HCID 59578067, compound

HRID 2194144Notes

Reaction equation

HRID 2194144 reaction equation
[F:1][C:2]([F:23])([F:22])[CH:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:15][CH2:14][C:13]3([CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)[C:12]2=[O:21])=[CH:7][CH:6]=1)[OH:4].[F:24][C:25]([F:38])([F:37])[O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[S:33](Cl)(=[O:35])=[O:34]>N1C=CC=CC=1>[F:23][C:2]([F:1])([F:22])[CH:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:15][CH2:14][C:13]3([CH2:16][CH2:17][N:18]([S:33]([C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=4[O:26][C:25]([F:24])([F:37])[F:38])(=[O:35])=[O:34])[CH2:19][CH2:20]3)[C:12]2=[O:21])=[CH:7][CH:6]=1)[OH:4]

Participants

4

Reactant 2

HCID 27772152-(Trifluoromethoxy)benzene-1-sulfonyl chlorideHCID 59578068HCID 59578068, compound

Product 1

HCID 59578067HCID 59578067, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Crude 2-[4-(2,2,2-trifluoro-1-hydroxy-ethyl)-phenyl]-2,8-diaza-spiro[4.5]decan-1-one from step A) (0.327 g) dissolved in pyridine at RT and under an argon atmosphere was treated with 2-trifluoromethoxy-benzenesulfonyl chloride (0.286 g) and the mixture was then stirred at RT over night. Then the most of pyridine was evaporated off in vacuo, the residue was dissolved in AcOEt which was then washed with 1M aqueous HCl and brine, dried over magnesium sulphate and concentrated in vacuo. The crude product was chromatographed over silica gel (eluent: AcOEt/Heptane, gradient from 0 to 30%) to give the desired product as a light brown solid. MS (ESI): 553.12 (MH+).

Workup

  1. customThen the most of pyridine was evaporated off in vacuo
  2. dissolutionthe residue was dissolved in AcOEt which
  3. washwas then washed with 1M aqueous HCl and brine
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe crude product was chromatographed over silica gel (eluent: AcOEt/Heptane, gradient from 0 to 30%)

Sources & evidence

ORD record
ord-9ee026cd2e0243e2b26f6a4d2d8b304d
Source dataset
uspto-grants-2012_12
Patent number
US08329904B2

Reaction notes

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