Trifluoroacetic acid → HCID 69742721, compound

HRID 1760370Notes

Reaction equation

HRID 1760370 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:10][CH2:9][CH2:8][N:7]1[C:11]1[CH:12]=[N:13][C:14]([O:17][C:18]2[CH:23]=[CH:22][C:21]([CH:24]=O)=[CH:20][CH:19]=2)=[CH:15][CH:16]=1)=[O:5])[CH3:2].[C:31]([O:35][C:36]([NH-:38])=[O:37])([CH3:34])([CH3:33])[CH3:32].C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C(OCC)(=O)C.C(#N)C>[CH2:1]([O:3][C:4]([C:6]1([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:10][CH2:9][CH2:8][N:7]1[C:11]1[CH:12]=[N:13][C:14]([O:17][C:18]2[CH:19]=[CH:20][C:21]([CH2:24][NH:38][C:36]([O:35][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:37])=[CH:22][CH:23]=2)=[CH:15][CH:16]=1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 86588174HCID 86588174, compoundHCID 178450610HCID 178450610, compound

Product 1

HCID 69742721HCID 69742721, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-[6-(4-Formyl-phenoxy)-pyridin-3-yl]-pyrrolidine-2,2-dicarboxylic acid diethyl ester (0.1 g, 0.24 mmol), tert-butoxycarbonylamide (0.083 g, 0.71 mmol), triethylsilane (0.11 mL, 0.083 g, 0.71 mmol) and acetonitrile (1 mL) was treated with trifluoroacetic acid (0.035 mL, 0.46 mmol) and stirred for 48 at ambient temperature. The mixture was diluted with ethyl acetate, washed with saturated sodium bicarbonate solution, brine, dried over sodium sulphate, filtered and concentrated in vacuo, affording 1-{6-[4-(tert-Butoxycarbonylamino-methyl)-phenoxy]-pyridin-3-yl}-pyrrolidine-2,2-dicarboxylic acid diethyl ester as a colorless syrup.

Workup

  1. washwashed with saturated sodium bicarbonate solution, brine
  2. dry with materialdried over sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-620d53095fc64867a46c9a4de105018b
Source dataset
uspto-grants-2005_01
Patent number
US06841671B2

Reaction notes

Loading…