Triethylamine → HCID 57519012, compound

HRID 2109326Notes

Reaction equation

HRID 2109326 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([N:19]([CH3:27])[C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:16][CH2:17]O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:28]([N:30](CC)CC)C.CS(Cl)(=O)=O.C1OCCOCCOCCOCCOC1.[C-]#N.[Na+]>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([N:19]([CH3:27])[C:20](=[O:26])[O:21][C:22]([CH3:24])([CH3:23])[CH3:25])[CH2:16][CH2:17][C:28]#[N:30])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 8929Sodium CyanideHCID 31297Methanesulfonyl chlorideHCID 3633615-Crown-5HCID 57519011HCID 57519011, compound

Product 1

HCID 57519012HCID 57519012, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

t-Butyl N-[1-(4-benzyloxyphenyl)-3-hydroxypropyl]-N-methylcarbamate (1.50 g, 4.0 mmol) obtained from Example 115b was dissolved in tetrahydrofuran (20 ml) under an atmosphere of nitrogen. To the solution was added triethylamine (0.84 ml, 6.0 mmol) and then methanesulfonyl chloride (0.37 ml, 4.8 mmol), in an ice bath. The resulting mixture was stirred at room temperature for 30 minutes. The reaction mixture was partitioned between water and ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was dissolved in N,N-dimethylformamide (20 ml) and to the solution was added 15-crown-5 (1.2 ml, 6.0 mmol) and then sodium cyanide (294 mg, 6.0 mmol). The resulting mixture was stirred at room temperature overnight. The reaction mixture was partitioned between water and ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using hexane:ethyl acetate=80:20 to 70:30 as the eluent to afford the desired compound (1.41 g).

Workup

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in N,N-dimethylformamide (20 ml) and to the solution
  6. stirringThe resulting mixture was stirred at room temperature overnight
  7. customThe reaction mixture was partitioned between water and ethyl acetate
  8. washThe organic layer was washed with saturated aqueous sodium chloride solution
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-aa854970c523428ba4cae3595cbeac4e
Source dataset
uspto-grants-2009_04
Patent number
US07514475B2

Reaction notes

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