Sodium hydride → HCID 70034929, compound

HRID 1861981Notes

Reaction equation

HRID 1861981 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][C:10](=[O:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[Br:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][Si:25]([C:38]([CH3:41])([CH3:40])[CH3:39])([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:20][C:19]=1[CH2:42]OS(C)(=O)=O>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:42][C:19]2[CH:20]=[C:21]([O:24][Si:25]([C:38]([CH3:40])([CH3:39])[CH3:41])([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:22]=[CH:23][C:18]=2[Br:17])[C:10](=[O:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 3157178Tert-butyl 3-oxopiperazine-1-carboxylateHCID 23001285HCID 23001285, compound

Product 1

HCID 70034929HCID 70034929, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution piperazin-3-one-1-carboxylic acid tert-butyl ester (2.11 g, 10.5 mmol) in dry DMEF (20 mL) at 0° C. was added sodium hydride (60% dispersion in mineral oil, 632 mg, 15.8 mmol). The reaction mixture was stirred for 1 hour, and then a solution of the mesylate from Step C (5.47 g, 10.5 mmol) in DMF (10 mL) was added. The reaction mixture was stirred for 16 hours. The solvent was removed in vacuo and the residue partitioned between methylene chloride (100 mL) and saturated aqueous sodium bicarbonate (100 mL). The layers were separated and the aqueous layer was extracted with methylene chloride (3×100 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. The crude product was purified by column chromatography (20→50% ethyl acetate/hexane) to provide the title compound as a yellow oil.

Workup

  1. stirringThe reaction mixture was stirred for 16 hours
  2. customThe solvent was removed in vacuo
  3. customthe residue partitioned between methylene chloride (100 mL) and saturated aqueous sodium bicarbonate (100 mL)
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with methylene chloride (3×100 mL)
  6. dry with materialThe combined organic layers were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by column chromatography (20→50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-8e4936fdfa30401bb17f92d2278a32c8
Source dataset
uspto-grants-2003_03
Patent number
US06534506B2

Reaction notes

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