Water → HCID 21838184, compound

HRID 1740313Notes

Reaction equation

HRID 1740313 reaction equation
[CH3:1][N:2]([CH3:19])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[CH:9]=[C:10]([CH:15]=[C:16]([OH:18])[CH:17]=1)[C:11]([O:13][CH3:14])=[O:12])=[O:7].N1C(C)=CC=CC=1C.[F:28][C:29]([F:42])([F:41])[S:30]([O:33]S(C(F)(F)F)(=O)=O)(=[O:32])=[O:31].O>CN(C)C1C=CN=CC=1.ClCCl>[F:28][C:29]([F:42])([F:41])[S:30]([OH:33])(=[O:32])=[O:31].[CH3:19][N:2]([CH3:1])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[CH:9]=[C:10]([CH:15]=[C:16]([O:18][S:30]([C:29]([F:42])([F:41])[F:28])(=[O:32])=[O:31])[CH:17]=1)[C:11]([O:13][CH3:14])=[O:12])=[O:7]

Participants

7

Reactant 4

HCID 962WaterHCID 79372,6-LutidineHCID 67749Trifluoromethanesulfonic anhydrideHCID 21837985HCID 21837985, compound

Product 1

HCID 21838184HCID 21838184, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of methyl 3-[(2-dimethylaminoethyl)carbamoyl]-5-hydroxybenzoate (11.9 g), 2,6-lutidine (6.25 ml) and 4-(dimethylamino)pyridine (0.84 g) in dichloromethane (240 ml) was added dropwise trifluoromethanesulfonic anhydride (9.02 ml) at -30° C. over 30 minutes. After stirring at room temperature for 4 hours, water (100 ml) was added to the reaction mixture. Two phases were separated and the aqueous layer was extracted with dichloromethane. The organic layers were combined, washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue was triturated with diethyl ether and the crystalline was collected and washed with diethyl ether to give methyl 3-[(2-dimethylaminoethyl)carbamoyl]-5-trifluoromethylsulfonyloxybenzoate trifluoromethanesulfonate (16.02 g).

Workup

  1. customTwo phases were separated
  2. extractionthe aqueous layer was extracted with dichloromethane
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was triturated with diethyl ether
  7. customthe crystalline was collected
  8. washwashed with diethyl ether

Sources & evidence

ORD record
ord-40041c10750542a3a3fb56b1471af05f
Source dataset
uspto-grants-1999_10
Patent number
US05968985

Reaction notes

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