Sodium bis(trimethylsilyl)amide → HCID 18626427, compound

HRID 2303340Notes

Reaction equation

HRID 2303340 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:16])[CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.C[Si](C)(C)[N-][Si](C)(C)C.[Na+].I[CH2:28][C:29]([CH:31]1[CH2:36][CH2:35][N:34]([C:37]([O:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[O:38])[CH2:33][CH2:32]1)=[O:30]>CS(C)=O.O1CCCC1.C(OCC)(=O)C>[CH2:40]([O:39][C:37]([N:34]1[CH2:35][CH2:36][CH:31]([C:29](=[O:30])[CH2:28][CH:9]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[O:16])[CH2:32][CH2:33]1)=[O:38])[C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1

Participants

7

Reactant 3

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 103308811-(4-Fluorophenyl)-2-(pyridin-4-yl)ethan-1-oneHCID 18626414HCID 18626414, compound

Product 1

HCID 18626427HCID 18626427, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the product of Step 1 (0.5 g (2.3 mmol)) in 5.0 ml of dry dimethyl sulfoxide was added 2.4 ml (2.4 mmol) of a 1M solution of sodium hexamethyldisilazide in tetrahydrofuran. After 10 minutes, a solution of 0.72 g (2.4 mmol) of the product of 4-(2-iodoacetyl)-1-(benzyloxycarbonyl)piperidine was added in 1 ml dimethyl sulfoxide dropwise. The reaction mixture was stirred for 2 hours, diluted with ethyl acetate (EtOAc, 20 ml) and washed with water (3×10 ml). The combined organic phases were washed with brine and dried over MgSO4. The mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified by MPLC over silica gel eluting with 2% MeOH/CH2Cl2 to give the desired product. FAB ms: C28H27N2O4F:474; Observed: 475 (M++1).

Workup

  1. washwashed with water (3×10 ml)
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationThe mixture was filtered
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe residue was purified by MPLC over silica gel eluting with 2% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-eee4d27531e448099e8a012ad85c6384
Source dataset
uspto-grants-2002_08
Patent number
US06432980B1

Reaction notes

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