Methyl morpholine oxide → (S)-N-(2-methoxybenzyl)-N-methyl-2-[N'-(t-butoxycarbonyl)-2-oxo-ethylamino]-3-phenyl-propionamide

HRID 1379961Notes

Reaction equation

HRID 1379961 reaction equation
[CH3:1][O:2][C:3]1[CH:32]=[CH:31][CH:30]=[CH:29][C:4]=1[CH2:5][N:6]([CH3:28])[C:7](=[O:27])[C@@H:8]([N:16]([CH2:24][CH:25]=C)[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C[N+]1([O-])CC[O:37]CC1.S(=O)(O)[O-].[Na+].C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Pb+4].C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl.[Os](=O)(=O)(=O)=O.O.CC(C)=O>[CH3:1][O:2][C:3]1[CH:32]=[CH:31][CH:30]=[CH:29][C:4]=1[CH2:5][N:6]([CH3:28])[C:7](=[O:27])[C@@H:8]([N:16]([CH2:24][CH:25]=[O:37])[C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

10

Reactant 5

HCID 82029Methyl morpholine oxideHCID 516892Sodium BicarbonateHCID 23665763Sodium BisulfiteHCID 86750260(S)-N-(2-Methoxybenzyl)-N-methyl-2-[N'-(t-butoxycarbonyl)-allylamino]-3-phenyl-propionamideHCID 178418268HCID 178418268, compound

Product 1

HCID 86750254(S)-N-(2-methoxybenzyl)-N-methyl-2-[N'-(t-butoxycarbonyl)-2-oxo-ethylamino]-3-phenyl-propionamide

Reagents, catalysts & solvents 4

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolventHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

Combine (S)-N-(2-methoxybenzyl)-N-methyl-2-[N'-(t-butoxycarbonyl)-allylamino]-3-phenyl-propionamide (0.66 g, 1.52 mmol), N-methylmorpholine-N-oxide (0.20 g, 1.67 mmol), acetone (5 mL), and water (5 mL). Add osmium tetraoxide (0.78 mL, 0.04M in THF, 0.032 mmol) and stir under an inert atmosphere for 18 hours. Pour the reaction mixture into a saturated solution of sodium bisulfite and extract the intermediate diol into ethyl acetate. Dry the separated organic layer over MgSO4, filter, and evaporate in vacuo to give the crude diol which is taken on to the next step without further purification. Dissolve the crude diol in chloroform (10 mL). Add a solution of lead tetraacetate (0.74 g, 1.67 mmol) in chloroform (10 mL). Stir for 30 minutes and then pour the reaction mixture into a saturated solution of sodium bicarbonate. Extract with dichloromethane and separate the organic layer. Dry the separated organic layer over MgSO4, filter and evaporate in vacuo to give the title compound which may be used without further purification.

Workup

  1. extractionextract the intermediate diol into ethyl acetate
  2. dry with materialDry the separated organic layer over MgSO4
  3. filtrationfilter
  4. customevaporate in vacuo
  5. customto give the crude diol which
  6. customis taken on to the next step without further purification
  7. dissolutionDissolve the crude diol in chloroform (10 mL)
  8. extractionExtract with dichloromethane
  9. customseparate the organic layer
  10. dry with materialDry the separated organic layer over MgSO4
  11. filtrationfilter
  12. customevaporate in vacuo

Sources & evidence

ORD record
ord-d6566c3ff174416ea6f38b0fcdc8722a
Source dataset
uspto-grants-1997_09
Patent number
US05672602

Reaction notes

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