Trifluoroacetic acid → HCID 178517285, compound

HRID 1294832Notes

Reaction equation

HRID 1294832 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([OH:8])[CH2:4][CH2:3]1.C1N=CN([C:14](N2C=NC=C2)=[O:15])C=1.[CH:21]1([O:26][C:27]2[CH:32]=[CH:31][C:30]([NH:33][CH2:34][CH:35](OCC)OCC)=[CH:29][CH:28]=2)[CH2:25][CH2:24][CH2:23][CH2:22]1.C(O)(C(F)(F)F)=O>O.CN(C=O)C>[CH:21]1([O:26][C:27]2[CH:28]=[CH:29][C:30]([N:33]3[CH:34]=[CH:35][N:1]([C@H:2]4[CH2:7][CH2:6][C@H:5]([OH:8])[CH2:4][CH2:3]4)[C:14]3=[O:15])=[CH:31][CH:32]=2)[CH2:22][CH2:23][CH2:24][CH2:25]1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 682631,1'-CarbonyldiimidazoleHCID 69151237HCID 69151237, compoundHCID 178511715HCID 178511715, compound

Product 1

HCID 178517285HCID 178517285, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Trans-4-aminocyclohexanol was reacted by method B with CDI and (4-cyclopentyloxyphenyl)(2,2-diethoxyethyl)amine. The isolated crude product was mixed with DMF (2 ml) and TFA (2 ml) and left to stand for 12 hours. The reaction solution was diluted with water, and the mixture was extracted with ethyl acetate. The organic phase was dried over magnesium sulfate, filtered and concentrated. The residue was purified by preparative HPLC. The product with the molecular weight of 342.44 (C20H26N2O3) was obtained in this way; MS (ESI): 343 ([M+H]+).

Workup

  1. customThe isolated crude product
  2. waitleft
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by preparative HPLC
  8. customThe product with the molecular weight of 342.44 (C20H26N2O3) was obtained in this way

Sources & evidence

ORD record
ord-0bcfb34cd8a04ca5902c83390a9af8b8
Source dataset
uspto-grants-2007_07
Patent number
US07241787B2

Reaction notes

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