Trifluoroacetic acid → HCID 22119938, compound

HRID 1274612Notes

Reaction equation

HRID 1274612 reaction equation
[C:1]([CH:4]([CH2:12][C:13]1[C:17]2[CH:18]=[C:19]([N:22]3[C:27](=[O:28])[CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[N:24]([CH3:33])[C:23]3=[O:34])[CH:20]=[CH:21][C:16]=2[S:15][N:14]=1)C(OC(C)(C)C)=O)(=[O:3])[CH3:2].FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:33][N:24]1[C:25]([C:29]([F:30])([F:31])[F:32])=[CH:26][C:27](=[O:28])[N:22]([C:19]2[CH:20]=[CH:21][C:16]3[S:15][N:14]=[C:13]([CH2:12][CH2:4][C:1](=[O:3])[CH3:2])[C:17]=3[CH:18]=2)[C:23]1=[O:34]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22119859HCID 22119859, compound

Product 1

HCID 22119938HCID 22119938, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl α-acetyl-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-propionate (0.700 g) and trifluoroacetic acid (10.0 mL) in methylene chloride is stirred overnight at room temperature, concentrated in vacuo, and diluted with methylene chloride and saturated sodium hydrogen carbonate solution. The phases are separated. The organic phase is dried over anhydrous magnesium sulfate and concentrated in vacuo to give 1-methyl-3-[3-(3-oxobutyl)-1,2-benzisothiazol-5-yl]-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione as a white solid (0.310 g, mp 198-199° C.). The aqueous phase is acidified with concentrated hydrochloric acid, stirred for several minutes, and filtered to obtain a solid. The solid is washed with water and air-dried to give α-acetyl-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-propionic acid as a white solid, mp 191-193° C.

Workup

  1. concentrationconcentrated in vacuo
  2. additiondiluted with methylene chloride and saturated sodium hydrogen carbonate solution
  3. customThe phases are separated
  4. dry with materialThe organic phase is dried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7c01316c5fbc4fba915ef2c6ea62ee23
Source dataset
uspto-grants-2000_12
Patent number
US06156700

Reaction notes

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