Dichloromethane → HCID 57827164, compound

HRID 1693213Notes

Reaction equation

HRID 1693213 reaction equation
ClCCl.[C:4]([NH:12][C:13]([NH:15][C@@:16]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[F:32])[CH2:21][C@@H:20]([O:22][CH3:23])[CH2:19][CH2:18][C@H:17]1[CH2:24]O)=[S:14])(=[O:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.N1C=CC=CC=1>[F:32][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[C@:16]12[CH2:21][C@@H:20]([O:22][CH3:23])[CH2:19][CH2:18][C@H:17]1[CH2:24][S:14][C:13]([NH:12][C:4](=[O:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[N:15]2

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 67749Trifluoromethanesulfonic anhydrideHCID 516892Sodium BicarbonateHCID 57827635HCID 57827635, compound

Product 1

HCID 57827164HCID 57827164, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

Dichloromethane (20 mL) and pyridine (264 μL, specific gravity: 0.978 g/cm3) were added to (±)-1-benzoyl-3-[(1S*,2R*,5S*)-1-(2-fluorophenyl)-2-hydroxymethyl-5-methoxycyclohexyl]thiourea obtained in Preparation Example 57-(6) (453 mg) according to the method of Preparation Example 18-(5). The mixture was cooled to −78° C. under a nitrogen atmosphere and stirred for 15 minutes. Trifluoromethanesulfonic anhydride (358 μL, specific gravity: 1.72 g/cm3) was slowly added to the reaction solution. After completion of the addition, the mixture was stirred for 15 minutes and then further stirred for one hour while warming to 0° C. After adding ethyl acetate, a saturated sodium bicarbonate solution was added, followed by extraction with ethyl acetate. The organic layer was sequentially washed with water and brine and dried over anhydrous magnesium sulfate. The solid was removed by filtration. After concentration under reduced pressure, the residue was purified by silica gel column chromatography to obtain the title compound (268 mg).

Workup

  1. additionAfter completion of the addition
  2. stirringthe mixture was stirred for 15 minutes
  3. stirringfurther stirred for one hour
  4. temperaturewhile warming to 0° C
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe organic layer was sequentially washed with water and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solid was removed by filtration
  9. concentrationAfter concentration under reduced pressure
  10. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c88e3c8ad7ee44fb949fbd8e17d1b90a
Source dataset
uspto-grants-2012_04
Patent number
US08158620B2

Reaction notes

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