Iodoethane → HCID 69145774, compound

HRID 2114845Notes

Reaction equation

HRID 2114845 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1([CH2:15][N:16]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].I[CH2:33][CH3:34]>CN(C=O)C>[CH2:1]([O:8][C:9]([N:11]([CH2:33][CH3:34])[C:12]1([CH2:15][N:16]([C:23]([O:25][C:26]([CH3:28])([CH3:27])[CH3:29])=[O:24])[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:13][CH2:14]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 69318084HCID 69318084, compound

Product 1

HCID 69145774HCID 69145774, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl N-[(1-{[(benzyloxy)carbonyl]amino}cyclopropyl)methyl]-N-(tert-butoxycarbonyl)glycinate (1.6 g, 3.94 mmol) in DMF (23 mL) at 0° C. under an atmosphere of nitrogen was added NaH (60% dispersion in oil, 19 mg, 7.87 mmol). The mixture was stirred for 40 min until gas evolution ceased. To the reaction was added iodoethane (346 μL, 4.33 mmol), followed stirring at room temperature for 3 h. The reaction was quenched with water, and DMF was removed in vacuo. The resulting aqueous mixture was extracted twice each with EtOAc and CH2Cl2. The combined organics were dried over Na2SO4, filtered, and concentrated in vacuo to afford a pale yellow, sticky solid. The crude product was subjected to column chromatography eluting with a gradient of 0-50% EtOAc/hexanes. Collection and concentration of the appropriate fractions afforded the product as a colorless oil.

Workup

  1. stirringfollowed stirring at room temperature for 3 h
  2. customThe reaction was quenched with water, and DMF
  3. customwas removed in vacuo
  4. extractionThe resulting aqueous mixture was extracted twice each with EtOAc and CH2Cl2
  5. dry with materialThe combined organics were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto afford a pale yellow, sticky solid
  9. washeluting with a gradient of 0-50% EtOAc/hexanes
  10. customCollection and concentration of the appropriate fractions

Sources & evidence

ORD record
ord-e8eef4c900a948ff82c39cfeb7e3f81a
Source dataset
uspto-grants-2008_10
Patent number
US07435735B2

Reaction notes

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