Ammonium Chloride → 2-Benzyloxycarbonylamino-1-phenyl-3-butene

HRID 1071366Notes

Reaction equation

HRID 1071366 reaction equation
[CH2:1]([Li])CCC.[C:6]([NH:16][C@H:17]([CH:25]=O)[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7].[NH4+].[Cl-]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[CH2:9]([O:8][C:6]([NH:16][CH:17]([CH:25]=[CH2:1])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:7])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 7021150Cbz-L-PhenylalaninalHCID 178418339Butyllithium

Product 1

HCID 136065862-Benzyloxycarbonylamino-1-phenyl-3-butene

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred suspension of methyltriphenylphosphonium bromide (10.72 g, 0.03 moles) in 100 mL of dry tetrahydofuran at −78° C. was added dropwise 1.6M n-butyl lithium (17.5 mL, 0.028 moles), and the mixture was stirred for 0.5 hrs at −78˜−20° C. Then was added a solution of N-Cbz-phenylalaninal (5.67 g, 0.02 moles) in 50 mL of dry tetrahydrofuran, and the mixture was stirred for 16 hrs at room temperature. After addition of saturated NH4Cl (50 mL) the mixture was extracted with EtOAc, and the extract was washed with water and brine. It was dried over Na2SO4 and evaporated to give an oily residue. The crude product was purified by column chromatograpy on silica gel with elution by 5:95 EtOAc-hexane to give pure 2-benzyloxycarbonylamino-1-phenyl-3-butene. Part B: Preparation of 2-benzyloxycarbonylamino-1-phenyl-3,4-epoxy-butane.

Workup

  1. stirringthe mixture was stirred for 16 hrs at room temperature
  2. extractionwas extracted with EtOAc
  3. washthe extract was washed with water and brine
  4. dry with materialIt was dried over Na2SO4
  5. customevaporated
  6. customto give an oily residue
  7. customThe crude product was purified by column chromatograpy on silica gel with elution by 5:95 EtOAc-hexane

Sources & evidence

ORD record
ord-cf340fa1d6234e62955529e3999cadb7
Source dataset
uspto-grants-2005_06
Patent number
US06906066B2

Reaction notes

Loading…