Potassium Fluoride → HCID 135446054, compound

HRID 1636009Notes

Reaction equation

HRID 1636009 reaction equation
[F-].[K+].[CH2:3]([C:5]1[N:6]([CH:31]2[CH2:34][N:33]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:32]2)[N:7]=[C:8]2[C:13](=[O:14])[NH:12][C:11]([C:15]3[C:16]([O:27][CH2:28][CH2:29][CH3:30])=[N:17][CH:18]=[C:19]([C:21]#[C:22][Si](C)(C)C)[CH:20]=3)=[N:10][C:9]=12)[CH3:4]>CN(C)C=O.C(OCC)(=O)C>[CH2:3]([C:5]1[N:6]([CH:31]2[CH2:34][N:33]([C:35]([O:37][C:38]([CH3:40])([CH3:39])[CH3:41])=[O:36])[CH2:32]2)[N:7]=[C:8]2[C:13](=[O:14])[NH:12][C:11]([C:15]3[C:16]([O:27][CH2:28][CH2:29][CH3:30])=[N:17][CH:18]=[C:19]([C:21]#[CH:22])[CH:20]=3)=[N:10][C:9]=12)[CH3:4]

Participants

5

Reactant 2

HCID 522689Potassium FluorideHCID 135530149HCID 135530149, compound

Product 1

HCID 135446054HCID 135446054, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Potassium fluoride (0.38 mmol) was added to a stirred solution of the product of stage f) (0.19 mmol) in aqueous N,N-dimethylformamide (2 ml N,N-dimethylformamide/0.2 ml water) at 0° C. After 10 min the reaction was allowed to warm to room temperature and stirred for 2 h. The reaction mixture was diluted with ethyl acetate and washed with water, 1 N hydrochloric acid (3 times) and brine. The organic layer was dried (MgSO4) and concentrated to give the title compound as a solid; 1H NMR (400MHz, CDCl3): δ=1.05 (t, 3H), 1.30 (t, 3H), 1.43 (s, 9H), 1.88-2.00 (m, 2H), 2H), 3.19 (s, 1H), 4.35 (app t, 2H), 4.52 (app t, 2H), 4.60-4.80 (br s, 2H), 5.22 (t, 1H), 8.39 (s, 1H), 8.80 (s, 1H), 10.75 (br s, 1H); LRMS (TSP—positive ion) 496 (MNH4+).

Workup

  1. washwashed with water, 1 N hydrochloric acid (3 times) and brine
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-be8aee59a49141d8b40edf6a58c181ef
Source dataset
uspto-grants-2003_01
Patent number
US06512002B2

Reaction notes

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