Trimethylsilyldiazomethane → HCID 56930596, compound

HRID 547118Notes

Reaction equation

HRID 547118 reaction equation
S(=O)(=O)(O)[O-].[K+].[C:7]([O:11][C:12]([NH:14][C@H:15]([C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)[C:16]([O-:18])=[O:17])=[O:13])([CH3:10])([CH3:9])[CH3:8].[CH:26]1([NH2+]C2CCCCC2)CCCCC1.C[Si](C=[N+]=[N-])(C)C>CCOCC>[CH3:26][O:17][C:16](=[O:18])[C@H:15]([NH:14][C:12]([O:11][C:7]([CH3:10])([CH3:8])[CH3:9])=[O:13])[C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 167693TrimethylsilyldiazomethaneHCID 516920Potassium bisulfateHCID 67065186HCID 67065186, compound

Product 1

HCID 56930596HCID 56930596, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A 0.5 N potassium bisulfate aqueous solution (7.9 mL) was added to a suspension of dicyclohexylammonium (R)-t-butoxycarbonylamino-(4-chloro-phenyl)acetate (605.6 mg, 1.30 mmol) in ether (16 mL), and the mixture was stirred for 10 minutes. Then, the aqueous layer was extracted with ether. The organic layer was washed with water and then brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was dissolved in benzene (3.6 mL) and methanol (1.8 mL). A solution of trimethylsilyldiazomethane in ether (2 M, 0.71 mL, 1.43 mmol) was added dropwise under cooling with ice, and then the mixture was stirred for 10 minutes. The reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate=4/1) to give the title compound (378.9 mg, 97%).

Workup

  1. extractionThen, the aqueous layer was extracted with ether
  2. washThe organic layer was washed with water
  3. dry with materialbrine, dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe resulting residue was dissolved in benzene (3.6 mL)
  6. temperatureunder cooling with ice
  7. stirringthe mixture was stirred for 10 minutes
  8. concentrationThe reaction mixture was concentrated under reduced pressure
  9. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-898e1e88e5d545a1a774a3f335850c3c
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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