Trifluoroacetic acid → HCID 131733365, compound

HRID 518933Notes

Reaction equation

HRID 518933 reaction equation
[Si:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]([C:53]2[CH:54]=[C:55]3[CH:61]=[CH:60][N:59]([CH3:62])[C:56]3=[N:57][CH:58]=2)[C:16]([C:18]2[CH:19]=[C:20]([C:27]3[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][C:28]=3[C:34]([N:36]3[C@H:45]([CH2:46][N:47]4[CH2:52][CH2:51][O:50][CH2:49][CH2:48]4)[CH2:44][C:43]4[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=4)[CH2:37]3)=[O:35])[N:21]3[C:26]=2[CH2:25][CH2:24][CH2:23][CH2:22]3)=[O:17])=[CH:11][CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:83][C:84]([N:86]1[CH2:91][CH2:90][CH2:89][CH2:88][CH2:87]1)=[O:85].N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O.FC(F)(F)C(O)=O>C1(C)C=CC=CC=1>[Si:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]([C:53]2[CH:54]=[C:55]3[CH:61]=[CH:60][N:59]([CH3:62])[C:56]3=[N:57][CH:58]=2)[C:16]([C:18]2[CH:19]=[C:20]([C:27]3[CH:32]=[CH:31][C:30]([O:33][CH2:83][C:84](=[O:85])[N:86]4[CH2:91][CH2:90][CH2:89][CH2:88][CH2:87]4)=[CH:29][C:28]=3[C:34]([N:36]3[C@H:45]([CH2:46][N:47]4[CH2:48][CH2:49][O:50][CH2:51][CH2:52]4)[CH2:44][C:43]4[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=4)[CH2:37]3)=[O:35])[N:21]3[C:26]=2[CH2:25][CH2:24][CH2:23][CH2:22]3)=[O:17])=[CH:11][CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

7

Reactant 5

HCID 6422Trifluoroacetic acidHCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 64804892-Hydroxy-1-(piperidin-1-yl)ethan-1-oneHCID 131733364HCID 131733364, compound

Product 1

HCID 131733365HCID 131733365, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

The compound of Step D (3.0 g, 2.9 mmol) is dissolved in 100 mL of toluene. 1.53 g (5.8 mmol) of triphenylphosphine and 0.62 g (4.3 mmol) of 2-hydroxy-1-(1-piperidyl)ethanone are added thereto. The mixture is heated to 50° C., and then 1.01 g (4.3 mmol) of di-tert-butyl azodicarboxylate are added. The reaction mixture is stirred at 50° C. for 1 hour and is then allowed to return to ambient temperature before adding 1 mL of trifluoroacetic acid. After stirring overnight at ambient temperature, the mixture is successively washed with water, saturated NaHCO3 and brine solution. The combined aqueous phases are extracted with ethyl acetate. The resulting organic phases are dried over sodium sulphate, filtered and concentrated under reduced pressure. The crude product obtained is purified by chromatography over silica gel (dichloromethane/ethanol 98/2) to yield the expected compound.

Workup

  1. customto return to ambient temperature
  2. stirringAfter stirring overnight at ambient temperature
  3. washthe mixture is successively washed with water, saturated NaHCO3 and brine solution
  4. extractionThe combined aqueous phases are extracted with ethyl acetate
  5. dry with materialThe resulting organic phases are dried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product obtained
  9. customis purified by chromatography over silica gel (dichloromethane/ethanol 98/2)

Sources & evidence

ORD record
ord-346dae02969e4883a7aab675b3feca46
Source dataset
uspto-grants-2015_08
Patent number
US09115159B2

Reaction notes

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