Trifluoroacetic acid → HCID 68325525, compound

HRID 2403282Notes

Reaction equation

HRID 2403282 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][O:18][C@@H:17]([C:21]2[CH:26]=[CH:25][C:24]([N:27]([C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=3)[CH3:28])=[CH:23][CH:22]=2)[CH2:16]1)=O)(C)(C)C.[OH-].[Na+]>O.C(#N)C>[Cl:35][C:32]1[CH:31]=[CH:30][C:29]([N:27]([CH3:28])[C:24]2[CH:23]=[CH:22][C:21]([C@@H:17]3[O:18][CH2:19][CH2:20][NH:15][CH2:16]3)=[CH:26][CH:25]=2)=[CH:34][CH:33]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 68325408HCID 68325408, compound

Product 1

HCID 68325525HCID 68325525, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of trifluoroacetic acid (51.3 μl) in water (4 ml) was added a solution of (S)-2-{4-[(4-chloro-phenyl)-methyl-amino]-phenyl}-morpholine-4-carboxylic acid tert-butyl ester (45 mg) in acetonitrile (2 ml). The reaction mixture was then capped and the mixture was shaken at 80° C. for 2 h. The reaction mixture was then cooled to room temperature and poured into 1 M aq. NaOH and the resulting mixture was extracted twice with EtOAc. The organic layers were dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash column chromatography (Isolute® Flash-NH2 from Separtis; gradient: 0% to 100% EtOAc in heptane, then 0% to 10% MeOH in EtOAc) to afford (4-chloro-phenyl)-methyl-((S)-4-morpholin-2-yl-phenyl)-amine (9 mg, 27%) as a colourless gum. MS (ISP): 305.3 ([{37Cl}M+H]+), 303.3 ([{35Cl}M+H]+).

Workup

  1. customThe reaction mixture was then capped
  2. temperatureThe reaction mixture was then cooled to room temperature
  3. extractionthe resulting mixture was extracted twice with EtOAc
  4. dry with materialThe organic layers were dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by flash column chromatography (Isolute® Flash-NH2 from Separtis

Sources & evidence

ORD record
ord-d45118dd790d4c3888eef1ffe599b0ef
Source dataset
uspto-grants-2014_08
Patent number
US08802673B2

Reaction notes

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