Trifluoroacetic acid → E-1210

HRID 1891520Notes

Reaction equation

HRID 1891520 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 3-1-2 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 out 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 out

Sources & evidence

ORD record
ord-cb82bfec9be247c8a517d2703e6690e2
Source dataset
uspto-grants-2013_08
Patent number
US08507530B2

Reaction notes

Loading…