Acetone → HCID 69321906, compound

HRID 448094Notes

Reaction equation

HRID 448094 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:22][CH3:23])=[C:6]([C:8](=[O:21])/[CH:9]=[C:10]2\[S:11][CH:12]=[C:13]([CH3:20])[N:14]\2[CH2:15][CH:16]2[CH2:19][CH2:18][CH2:17]2)[CH:7]=1.C([N-]C(C)C)(C)C.[Li+].[CH3:32][C:33]([CH3:35])=[O:34]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:22][CH3:23])=[C:6]([C:8](=[O:21])/[CH:9]=[C:10]2\[S:11][C:12]([C:33]([OH:34])([CH3:35])[CH3:32])=[C:13]([CH3:20])[N:14]\2[CH2:15][CH:16]2[CH2:17][CH2:18][CH2:19]2)[CH:7]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 2724682Lithium diisopropylamideHCID 69189523HCID 69189523, compound

Product 1

HCID 69321906HCID 69321906, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 169B (140 mg, 4 mmol) in tetrahydrofuran (4 mL) at −78° C. was added lithium diisopropylamide (2 M, 0.6 mL). Acetone (81 μL, 1.2 mmol) was added after 5 min. The reaction was quenched with saturated ammonium chloride (10 mL) after 10 min and the reaction mixture was allowed to warm to room temperature. The reaction was extracted with ethyl acetate (3×10 mL). The organics were combined, washed with brine, dried with sodium sulfate and concentrated. The residue was purified by chromatography over silica gel (dichloromethane-EtOAc 5:1 as eluent) to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.48 (s, 6 H) 1.80-1.93 (m, 4 H) 1.99-2.04 (m, 2 H) 2.35 (s, 3 H) 2.68-2.82 (m, 1 H) 3.86 (s, 3 H) 3.96 (d, J=6.78 Hz, 2 H) 5.49 (s, 1 H) 6.53 (s, 1 H) 7.10 (d, J=8.82 Hz, 1 H) 7.39 (dd, J=8.82, 2.71 Hz, 1 H) 7.63 (d, J=2.71 Hz, 1 H). MS (ESI) m/z 408 (M+H)+. Anal calcd for C21H26ClNO3S.0.7H2O: C, 59.97; H, 6.57; N, 3.33. Found: C, 59.76; H, 6.76; N, 3.02.

Workup

  1. customThe reaction was quenched with saturated ammonium chloride (10 mL) after 10 min
  2. extractionThe reaction was extracted with ethyl acetate (3×10 mL)
  3. washwashed with brine
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography over silica gel (dichloromethane-EtOAc 5:1 as eluent)

Sources & evidence

ORD record
ord-02f12662a6714249990c30c5a4b6aed3
Source dataset
uspto-grants-2013_07
Patent number
US08481574B2

Reaction notes

Loading…