Sodium hydride → HCID 66999488, compound

HRID 559353Notes

Reaction equation

HRID 559353 reaction equation
[H-].[Na+].[C:3]([O:7][C:8](=[O:20])[NH:9][C:10]1([C:13](=[O:19])[NH:14][CH2:15][CH2:16][CH:17]=[CH2:18])[CH2:12][CH2:11]1)([CH3:6])([CH3:5])[CH3:4].FC(F)(F)S(O[CH2:27][CH2:28]OS(C(F)(F)F)(=O)=O)(=O)=O>O1CCCC1>[C:3]([O:7][C:8]([N:9]1[CH2:28][CH2:27][N:14]([CH2:15][CH2:16][CH:17]=[CH2:18])[C:13](=[O:19])[C:10]21[CH2:12][CH2:11]2)=[O:20])([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 24758Sodium hydride2×HCID 11045622HCID 11045622, compound2×HCID 66999519HCID 66999519, compound

Product 1

HCID 66999488HCID 66999488, compoundYield 47.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium hydride (60% dispersion in mineral oil, 206 mg, 5.15 mmol) was added at 0° C. to a solution of (1-but-3-enylcarbamoyl-cyclopropyl)-carbamic acid tert-butyl ester (400 mg, 1.57 mmol) in tetrahydrofuran (8 ml), then after 15 min a solution of 1,2-bis(((trifluoromethyl)sulfonyl)oxy)ethane (Chem. Ber. 1981, 114, 810; 616 mg, 1.89 mmol) in tetrahydrofuran (1 ml) was added dropwise. After 1 h, another portion of sodium hydride (60% dispersion in mineral oil, 103 mg, 2.58 mmol) and after 15 min, 1,2-bis(((trifluoromethyl)sulfonyl)oxy)ethane (616 mg, 1.78 mmol) was added, and die reaction mixture was allowed to reach room temperature over 1 h, then partitioned between ethyl acetate and water. The organic layer was washed with brine, dried (MgSO4), and evaporated. Chromatography (SiO2; heptane-ethyl acetate gradient) produced the title compound (208 mg, 47%). Yellow oil, MS (ISP)=281.2 (M+H)+.

Workup

  1. customdie reaction mixture
  2. waitto reach room temperature over 1 h
  3. custompartitioned between ethyl acetate and water
  4. washThe organic layer was washed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-1728c939e31c4701b4b40e08d7c97dcf
Source dataset
uspto-grants-2011_11
Patent number
US08063042B2

Reaction notes

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