Dimethyl Sulfoxide → HCID 86686498, compound

HRID 239141Notes

Reaction equation

HRID 239141 reaction equation
CS(C)=O.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[OH:18][CH:19]1[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH:21]([CH3:33])[CH2:20]1.C(N(CC)CC)C>ClCCl.O>[CH3:33][CH:21]1[CH2:20][C:19](=[O:18])[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:30])([CH3:32])[CH3:31])=[O:27])[CH2:22]1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 86686496HCID 86686496, compound

Product 1

HCID 86686498HCID 86686498, compoundYield 27.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-78 °C

Procedure

A mixture of 46 mL DMSO and 500 mL dichlormethane was cooled to −78° C. and a solution of 68 mL, trifluoroacetic anhydride in 200 mL dichlormethane was added. Then, a solution of 50.6 g tert-butyl 5-hydroxy-3-methylazepane-1-carboxylat in 500 mL dichlormethane was added. The mixture was stirred at −78° C. for 1 h, 128 mL triethylamine was added and the mixture was warmed to RT. 1 L water was added and the layers were separated. The aqueous fraction was extracted two times with 500 mL dichlormethane. The combined organic fractions were dried, filtered and concentrated. Column chromatography on silica with ethyl acetate/heptane (1:4) yielded 13.7 g of the desired product. (M+H)+: 228

Workup

  1. temperaturethe mixture was warmed to RT
  2. customthe layers were separated
  3. extractionThe aqueous fraction was extracted two times with 500 mL dichlormethane
  4. customThe combined organic fractions were dried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6673396bed9d47658df2caa84af2d621
Source dataset
uspto-grants-2014_02
Patent number
US08642774B2

Reaction notes

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