Sodium hydride → HCID 14343476, compound

HRID 2184074Notes

Reaction equation

HRID 2184074 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:15])[CH2:7][NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:4].O([CH2:24][CH3:25])S(C(F)(F)F)(=O)=O>C1COCC1.C(OCC)(=O)C>[CH2:24]([N:8]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:7][C:6]([O:5][CH2:3][CH3:4])=[O:15])[CH3:25]

Participants

6

Reactant 3

HCID 24758Sodium hydride2×HCID 67924Ethyl trifluoromethanesulphonateHCID 75190N-Phenylglycine ethyl ester

Product 1

HCID 14343476HCID 14343476, compoundYield 17.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

NaH (224 mg, 5.6 mmol of 60% dispersion) was washed 3 times with hexanes and dried via vacuum aspiration. To the dry NaH was added a solution of N-phenylglycine ethyl ester (1 g, 5.6 mmol) in THF (28 mL) at 0° C. After stirring 1.5 h, ethyl triflate (0.7 mL, 5.6 mmol) was added via syringe. The resulting solution was stirred at ambient temperature over 18 h. The mixture was diluted with ethyl acetate and washed with 1M HCl and brine. The organics were dried (MgSO4) and concentrated in vacuo. Purification by flash chromatography (4:1 hexanes/EtOAc) afforded the title compound as a light yellow oil (200 mg, 17%). MS (ES+) m/z 208 (MH+).

Workup

  1. customdried via vacuum aspiration
  2. stirringThe resulting solution was stirred at ambient temperature over 18 h
  3. washwashed with 1M HCl and brine
  4. dry with materialThe organics were dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography (4:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-b526c673de304f639bffcdf615ddc13b
Source dataset
uspto-grants-2005_05
Patent number
US06900244B2

Reaction notes

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