4-Toluenesulfonyl chloride → HCID 24966915, compound

HRID 1092339Notes

Reaction equation

HRID 1092339 reaction equation
CC(C)([O-])C.[Na+].[CH:7]1([N:10]([CH:24]([CH2:28]O)[CH:25]([CH3:27])[CH3:26])[C:11]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:20]([F:23])([F:22])[F:21])=[O:12])[CH2:9][CH2:8]1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1>C1COCC1>[CH:7]1([N:10]2[CH:24]([CH:25]([CH3:27])[CH3:26])[CH2:28][N:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[C:20]([F:23])([F:22])[F:21])[C:11]2=[O:12])[CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 23676156Sodium t-butoxideHCID 57495607HCID 57495607, compound

Product 1

HCID 24966915HCID 24966915, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Following a procedure outlined in J. Org. Chem. 64, 1999, 2941-2943, sodium tert-butoxide (200 mg) and 1-cyclopropyl-1-(1-hydroxymethyl-2-methyl-propyl)-3-(2-trifluoromethyl-phenyl)-urea (245 mg) were added to THF (17 mL) and cooled to 0° C. To the mixture was added a solution of p-toluenesulfonyl chloride (170 mg) in THF (5 mL) slowly by syringe to give a suspension. The mixture was allowed to stir at RT for 12 hours and was then quenched by addition of ice cold water (15 mL). The mixture was extracted with ethyl acetate and the organic layer was separated, dried over Na2SO4 and evaporated. The crude material was purified by flash chromatography using ethyl acetate/heptane 1:1 as an eluent to give the desired material as yellow oil (170 mg). MS (ESI): 313.3 (MH+).

Workup

  1. customto give a suspension
  2. customwas then quenched by addition of ice cold water (15 mL)
  3. extractionThe mixture was extracted with ethyl acetate
  4. customthe organic layer was separated
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. customThe crude material was purified by flash chromatography

Sources & evidence

ORD record
ord-2c1fcc7ebf9f4d3d8a6ff3d30c25b7ca
Source dataset
uspto-grants-2012_03
Patent number
US08129423B2

Reaction notes

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