Cesium carbonate → HCID 69595822, compound

HRID 719389Notes

Reaction equation

HRID 719389 reaction equation
[CH2:1]([O:8][N:9]1[C@H:13]([CH:14]([CH3:16])[CH3:15])[CH2:12][C@@H:11]([NH:17][S:18]([C:21]2[CH:26]=[CH:25][C:24]([C:27]3[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=3)=[CH:23][CH:22]=2)(=[O:20])=[O:19])[C:10]1=[O:37])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I[CH2:39][CH2:40][CH3:41].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH2:1]([O:8][N:9]1[C@H:13]([CH:14]([CH3:16])[CH3:15])[CH2:12][C@@H:11]([N:17]([CH2:39][CH2:40][CH3:41])[S:18]([C:21]2[CH:26]=[CH:25][C:24]([C:27]3[CH:28]=[CH:29][C:30]([C:33]([F:34])([F:35])[F:36])=[CH:31][CH:32]=3)=[CH:23][CH:22]=2)(=[O:20])=[O:19])[C:10]1=[O:37])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 336431-IodopropaneHCID 69152452HCID 69152452, compound

Product 1

HCID 69595822HCID 69595822, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-[(3R,5S)-1-(Benzyloxy)-5-isopropyl-2-oxopyrrolidinyl]-4′-(trifluoromethyl)[1,1′-biphenyl]-4-sulfonamide (0.047 g, 0.088 mmoles, Example 27a), 1-iodopropane (0.052 mL, 0.53 mmoles), cesium carbonate (0.043 g, 0.13 mmoles) and anhydrous N,N-dimethylformamide (0.50 mL) was stirred at 55° C. (oil temperature) over night, concentrated by rotary evaporation, taken up diethylether and washed with water once. The aqueous phase was washed with a second portion of diethylether, the combined organic phases were washed with brine, dried with potassium carbonate, filtered and concentrated by rotary evaporation. Flash chromatography of the crude product on silica using dichloromethane-methanol (99:1) as eluent gave the title compound as a colourless oil. LC-MS (APCI) m/z 575 (M+1). 1H NMR (CDCl3) δ 8.12 (d, J=8 Hz, 2H), 7.74–7.69 (m, 5H), 7.72 (d, J=8 Hz, 2H), 7.44–7.34 (m, 4H), 5.01 (s, 2H), 4.48 (dd, J1=8 Hz, J2=10 Hz, 1H), 3.45 (dt, J1=3 Hz, J2=9 Hz, 1H), 3.10–2.98 (m, 2H), 2.24 (ddd, J1=2 Hz, J2=10 Hz, J3=14 Hz, 1H), 2.20–2.10 (m, 1H), 2.03 (dt, J1=9 Hz, J2=14 Hz, 1H), 1.73–1.51 (m, 2H), 0.87 (d, J=7 Hz, 3H), 0.84 (d, J=7 Hz, 3H) and 0.82 (obscured t, J=7 Hz, 3H) ppm.

Workup

  1. concentrationconcentrated by rotary evaporation
  2. washwashed with water once
  3. washThe aqueous phase was washed with a second portion of diethylether
  4. washthe combined organic phases were washed with brine
  5. dry with materialdried with potassium carbonate
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-ebf80377fd8f49d98eef723311e984c4
Source dataset
uspto-grants-2006_11
Patent number
US07132434B2

Reaction notes

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