Sodium hydride → HCID 117840819, compound

HRID 714890Notes

Reaction equation

HRID 714890 reaction equation
C(OC([NH:8][CH2:9][CH2:10][C:11]([CH:19]1[CH2:22][N:21]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:20]1)([C:17]#[N:18])[C:12](OCC)=[O:13])=O)(C)(C)C.[H-].[Na+].C(=O)([O-])O.[Na+]>O1CCCC1>[C:17]([C:11]1([CH:19]2[CH2:22][N:21]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:20]2)[CH2:10][CH2:9][NH:8][C:12]1=[O:13])#[N:18]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 117840653HCID 117840653, compound

Product 1

HCID 117840819HCID 117840819, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl 3-(4-((tert-butoxycarbonyl)amino)-2-cyano-1-ethoxy-1-oxobutan-2-yl)azetidine-1-carboxylate (7 g) obtained in Step B of Example 309 in tetrahydrofuran (80 mL) was added sodium hydride (60% in mineral oil, 816 mg) in an ice bath, and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (1.4 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe obtained organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-38516d98b00e4c909a6477e399280e2b
Source dataset
uspto-grants-2015_11
Patent number
US09187453B2

Reaction notes

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