Trifluoromethanesulfonic acid → HCID 178501161, compound

HRID 1893332Notes

Reaction equation

HRID 1893332 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11](=[O:21])[NH:12][CH2:13][CH:14](OCC)[O:15]CC)[CH2:7][CH2:6]1)=[O:4].FC(F)(F)S(O)(=O)=O>COCCOC>[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11](=[O:21])[NH:12][CH2:13][CH:14]=[O:15])[CH2:7][CH2:6]1)=[O:4]

Participants

4

Reactant 2

HCID 62406Trifluoromethanesulfonic acidHCID 178467960HCID 178467960, compound

Product 1

HCID 178501161HCID 178501161, compoundYield 108.9%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of trans-4-(2,2-diethoxy-ethylcarbamoyl)-cyclohexanecarboxylic acid methyl ester (900 mg, 2.99 mmol) and trifluoromethanesulfonic acid (996 mg, 4.48 mmol) in 1,2-dimethoxyethane (30 ml) was heated at 40° C. for 4 h. After cooling to room temperature the reaction mixture was partitioned between ethyl acetate (100 ml) and saturated aqueous sodium bicarbonate solution (50 ml). The layers were separated. The aqueous layer was extracted with two 100 ml-portions of ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound (740 mg, quantitative) as light brown viscous oil, which was used in the next step without further purifications. MS m/e: 228 ([M+H]+)

Workup

  1. customwas partitioned between ethyl acetate (100 ml) and saturated aqueous sodium bicarbonate solution (50 ml)
  2. customThe layers were separated
  3. extractionThe aqueous layer was extracted with two 100 ml-portions of ethyl acetate
  4. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7f57e8c28c0f48f1ab01010fb6226ef9
Source dataset
uspto-grants-2013_08
Patent number
US08513238B2

Reaction notes

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