2,2,2-Trifluoroethanol → HCID 22615031, compound

HRID 843135Notes

Reaction equation

HRID 843135 reaction equation
[CH3:1][C:2]1[C:6]2[C:7]([O:11][CH2:12][CH2:13][CH2:14][NH:15][CH2:16][C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[CH2:23][O:24][C:25]1[CH:26]=[CH:27][C:28]2[O:32][C:31]([CH2:33][OH:34])=[CH:30][C:29]=2[CH:35]=1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C(P(CCCC)CCCC)CCC.[F:67][C:68]([F:72])([F:71])[CH2:69]O>C1C=CC=CC=1>[CH3:1][C:2]1[C:6]2[C:7]([O:11][CH2:12][CH2:13][CH2:14][NH:15][CH2:16][C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[CH2:23][O:24][C:25]1[CH:26]=[CH:27][C:28]2[O:32][C:31]([CH2:33][O:34][CH2:69][C:68]([F:72])([F:71])[F:67])=[CH:30][C:29]=2[CH:35]=1

Participants

6

Reactant 4

HCID 64092,2,2-TrifluoroethanolHCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 22614988HCID 22614988, compound

Product 1

HCID 22615031HCID 22615031, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The compound of Example 40 (60 mg) and 1,1′-(azodicarbonyl)dipiperidine (64 mg) were suspended in dry benzene (2 ml). To the suspension was added tributylphosphine (63 μl) at room temperature. The mixture was stirred at room temperature for 15 minutes. To the mixture was added 2,2,2-trifluoroethanol (74 μl). The mixture was stirred at room temperature overnight. After removing the solvent the reaction mixture was separated by silica gel column chromatography developed by the solvent mixture of dichloromethane and methanol. The title compound (57 mg) was obtained as a colorless oil. ESI-MS: m/z 555 (MH+); 1H-NMR (CDCl3): δ 2.05 (2H, quintet, J=6.5 Hz), 2.33 (3H, s), 2.87 (2H, t, J=7 Hz), 3.83 (2H, s), 3.91 (2H, q, 8.5 Hz), 4.14 (2H, t, J=6 Hz), 4.74 (2H, s), 5.10 (2H, s), 6.60 (1H, d, J=7 Hz), 6.71 (1H,s), 6.95-7.25 (5H, m), 7.38 (1H, d, J=9 Hz), 7.66 (1H, dt, J=7.5 Hz, 2 Hz), 8.48 (1H, dd, J=1.5 Hz, 4.5 Hz), 8.56 (1H, d, J=1.5 Hz).

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. customAfter removing the solvent the reaction mixture
  3. customwas separated by silica gel column chromatography
  4. additiondeveloped by the solvent mixture of dichloromethane and methanol

Sources & evidence

ORD record
ord-c8b85715742244e08d3c92dfce4e3938
Source dataset
uspto-grants-2002_04
Patent number
US06376491B1

Reaction notes

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