Trifluoroacetic acid → E-1210

HRID 1930755Notes

Reaction equation

HRID 1930755 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[O:7][CH2:8][C:9]1[CH:41]=[CH:40][C:12]([CH2:13][C:14]2[CH:18]=[C:17]([C:19]3[C:20]([N:25](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)=[N:21][CH:22]=[CH:23][CH:24]=3)[O:16][N:15]=2)=[CH:11][CH:10]=1.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>ClCCl>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[O:7][CH2:8][C:9]1[CH:41]=[CH:40][C:12]([CH2:13][C:14]2[CH:18]=[C:17]([C:19]3[C:20]([NH2:25])=[N:21][CH:22]=[CH:23][CH:24]=3)[O:16][N:15]=2)=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 25114167Di-tert-butyl (3-(3-(4-((pyridin-2-yloxy)methyl)benzyl)isoxazol-5-yl)pyridin-2-yl)imidodicarbonate

Product 1

HCID 16719049E-1210Yield 96.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a dichloromethane (120 mL) solution of di-tert-butyl (3-(3-(4-((pyridin-2-yloxy)methyl)benzyl)isoxazol-5-yl)pyridin-2-yl)imidodicarbonate (11.8 g, purity about 70%) described in Manufacturing Example 1-4-2 was added trifluoracetic acid (40 mL) at 0° C., which was stirred at room temperature for 14 hours. To the reaction mixture was added saturated aqueous sodium bicarbonate at 20° C. or less, which was then extracted with ethyl acetate and purified by NH silica gel column chromatography (heptane:ethyl acetate=1:1). The solvent was concentrated under a reduced pressure, tert-butylmethyl ether was added to the resulting residue, and the solids were filtered to obtain the title compound (7.29 g).

Workup

  1. extractionwhich was then extracted with ethyl acetate
  2. custompurified by NH silica gel column chromatography (heptane:ethyl acetate=1:1)
  3. concentrationThe solvent was concentrated under a reduced pressure, tert-butylmethyl ether
  4. additionwas added to the resulting residue
  5. filtrationthe solids were filtered

Sources & evidence

ORD record
ord-987d99d518554d8789c466383a2962e7
Source dataset
uspto-grants-2012_05
Patent number
US08188119B2

Reaction notes

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