Sodium hydride → HCID 66605976, compound

HRID 1723710Notes

Reaction equation

HRID 1723710 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([NH:8][C@H:9]1[CH2:13][N:12]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:11][C@@H:10]1[NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:7].[H-].[Na+]>C1COCC1.CN(C=O)C>[CH2:14]([N:12]1[CH2:13][C@H:9]([N:8]2[CH2:2][CH2:3][CH2:4][CH2:5][C:6]2=[O:7])[C@@H:10]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:11]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 24758Sodium hydrideHCID 86617113HCID 86617113, compound

Product 1

HCID 66605976HCID 66605976, compoundYield 87.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product of Step 7 (6.3 g, 13.9 mmol) in THF (60 mL) and DMF (30 mL) was added sodium hydride (611 mg, 60% in oil, 15.29 mmol). After stirring the reaction mixture overnight at RT, it was quenched with water and extracted with EtOAc (3×100 mL). The combined extracts were washed with brine, dried over sodium sulfate, filtered, and concentrated to furnish the crude product. The residue was purified by column chromatography on silica gel (90:10 petroleum ether/EtOAc) to obtain desired product (4.53 g, 87.4%). 1H NMR (300 MHz, CDCl3) δ 5.38 (1H, s), 4.60 (1H, m), 4.18 (1H, s), 3.50-3.20 (6H, m), 3.00 (1H, m), 2.80 (1H, m), 2.40 (4H, m), 1.80 (4H, m), 1.40 (9H, m). MS m/z 374 (MH+).

Workup

  1. customit was quenched with water
  2. extractionextracted with EtOAc (3×100 mL)
  3. washThe combined extracts were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto furnish the crude product
  8. customThe residue was purified by column chromatography on silica gel (90:10 petroleum ether/EtOAc)

Sources & evidence

ORD record
ord-7cc5b8d59e4f460c8315f09d1920256e
Source dataset
uspto-grants-2009_02
Patent number
US07485641B2

Reaction notes

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