Trifluoroacetic acid → E-1210

HRID 557271Notes

Reaction equation

HRID 557271 reaction equation
C(OC([N:8]([C:16]1[C:21]([C:22]2[O:26][N:25]=[C:24]([CH2:27][C:28]3[CH:33]=[CH:32][C:31]([CH2:34][O:35][C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=4)=[CH:30][CH:29]=3)[CH:23]=2)=[CH:20][CH:19]=[CH:18][N:17]=1)C(OC(C)(C)C)=O)=O)(C)(C)C.FC(F)(F)C(O)=O.O.C(=O)(O)[O-].[Na+]>ClCCl>[N:37]1[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=1[O:35][CH2:34][C:31]1[CH:32]=[CH:33][C:28]([CH2:27][C:24]2[CH:23]=[C:22]([C:21]3[C:16]([NH2:8])=[N:17][CH:18]=[CH:19][CH:20]=3)[O:26][N:25]=2)=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 25114167Di-tert-butyl (3-(3-(4-((pyridin-2-yloxy)methyl)benzyl)isoxazol-5-yl)pyridin-2-yl)imidodicarbonateHCID 86585896Sodium bicarbonate water

Product 1

HCID 16719049E-1210

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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

Workup

  1. extractionlower, 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-butyl methyl ether
  4. additionwas added to the resulting residue, and solids
  5. filtrationwere filtered

Sources & evidence

ORD record
ord-b87a6374a89e4dac8b9ad0babfdc99b0
Source dataset
uspto-grants-2011_11
Patent number
US08058444B2

Reaction notes

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