Dimethylformamide → HCID 67642543, compound

HRID 1458963Notes

Reaction equation

HRID 1458963 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[NH:11][C:10]2=[O:18])=[CH:3][CH:2]=1.[CH3:19][Si]([N-][Si](C)(C)C)(C)C.[Na+].BrCC(O[C:34]([CH3:37])([CH3:36])[CH3:35])=O.CN([CH:41]=[O:42])C>>[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]([C:41](=[O:42])[CH2:19][C:34]([CH3:35])([CH3:36])[CH3:37])[C:10]2=[O:18])=[CH:3][CH:2]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 79177tert-Butyl bromoacetateHCID 2724254Sodium bis(trimethylsilyl)amideHCID 22097752HCID 22097752, compound

Product 1

HCID 67642543HCID 67642543, compound

Procedure

A solution of 20-3 (3.55 g, 14.8 mmol) in DMF (50 mL) was treated dropwise with NaN(TMS)2 (16.3 mL, 1.0M in THF), the solution was stirred for 45 minutes, then treated with t-butyl bromoacetate (2.7 mL, 17 mmol) and stirred for 30 minutes. The reaction was quenched with H2O and the solvents were removed in vacuo. The residue was chromatographed (silica gel, 50% acetone/Hexanes) to give 20-4 as a oily, yellow solid.

Workup

  1. stirringstirred for 30 minutes
  2. customThe reaction was quenched with H2O
  3. customthe solvents were removed in vacuo
  4. customThe residue was chromatographed (silica gel, 50% acetone/Hexanes)
  5. customto give 20-4 as a oily, yellow solid

Sources & evidence

ORD record
ord-96ea546dcbb343fc91f6bae588b2308f
Source dataset
uspto-grants-1998_12
Patent number
US05852045

Reaction notes

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