HCID 178484015, compound → HCID 178484017, compound

HRID 967129Notes

Reaction equation

HRID 967129 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([CH2:12][N:13]([CH3:27])[S:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:8][CH2:7]1>N1C=CC=CC=1>[CH3:27][N:13]([CH2:12][C@H:9]1[CH2:8][CH2:7][C@H:6]([CH2:5][CH2:4][CH2:3][CH2:2][O:1][S:14]([CH3:17])(=[O:16])=[O:15])[CH2:11][CH2:10]1)[S:14]([C:17]1[CH:18]=[CH:19][C:20]([C:23]([F:26])([F:24])[F:25])=[CH:21][CH:22]=1)(=[O:16])=[O:15]

Participants

3

Reactant 1

HCID 178484015HCID 178484015, compound

Product 1

HCID 178484017HCID 178484017, compoundYield 185.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
-10 °C

Procedure

1.22 g (3.0 mmol) trans-N-[4-(4-hydroxy-butyl)-cyclohexylmethyl]-N-methyl-4-trifluoromethyl-benzenesulfonamide were dissolved in 4.0 ml of pyridine, cooled to −10° C. and treated with 0.687 g methanesulfochloride. The reaction mixture was then stirred at room temperature for 2 hours. It was subsequently poured into 50 ml of an ice/water/diluted hydrogen chloride mixture and extracted 3 times with 50 ml of dichloromethane. The combined dichloromethane phases were dried over magnesium sulfate and evaporated under reduced pressure giving 1.35 g (92.8%) trans-methanesulfonic acid 4-(4-{[methyl-(4-trifluoromethyl-benzenesulfonyl)-amino]-methyl}-cyclohexyl)-butyl ester as colorless solid, MS: 486 (MH+).

Workup

  1. additiontreated with 0.687 g methanesulfochloride
  2. extractionextracted 3 times with 50 ml of dichloromethane
  3. dry with materialThe combined dichloromethane phases were dried over magnesium sulfate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-8281154f619748ab9784902799af3d43
Source dataset
uspto-grants-2005_10
Patent number
US06953806B2

Reaction notes

Loading…