4-Methylmorpholine → N-((1,1-Dimethylethoxy)carbonyl)-4-iodo-D-phenylalanine methyl ester

HRID 747733Notes

Reaction equation

HRID 747733 reaction equation
S(Cl)(Cl)=O.[CH:5]1[C:10]([CH2:11][C@@H:12]([NH2:16])[C:13]([OH:15])=[O:14])=[CH:9][CH:8]=[C:7]([I:17])[CH:6]=1.[CH3:18]N1CCOCC1.[C:25](=O)([O:31]C(C)(C)C)[O:26][C:27]([CH3:30])([CH3:29])[CH3:28]>O.ClCCl.CO>[C:27]([O:26][C:25]([NH:16][C@H:12]([CH2:11][C:10]1[CH:9]=[CH:8][C:7]([I:17])=[CH:6][CH:5]=1)[C:13]([O:15][CH3:18])=[O:14])=[O:31])([CH3:30])([CH3:29])[CH3:28]

Participants

8

Reactant 4

HCID 79724-MethylmorpholineHCID 24386Thionyl ChlorideHCID 27332794-Iodo-D-phenylalanineHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

Product 1

HCID 53885913N-((1,1-Dimethylethoxy)carbonyl)-4-iodo-D-phenylalanine methyl ester

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

17 ml (230 mmol) of thionyl chloride was added to 3 ml of methanol under cooling with ice. 22.2 g (76.3 mmol) of D-4-iodophenylalanine was added to the resultant mixture, and they were heated under reflux for 2 hours. The solvent was evaporated. 15 ml (137 mmol) of N-methylmorpholine, 12 g (55 mmol) of di-t-butyl carbonate and 100 ml of dichloromethane were added to the residue, and they were stirred for 19 hours. The reaction liquid was diluted with water. After the extraction with dichloromethane, the organic layer was successively washed with saturated aqueous sodium hydrogencarbonate solution and saturated aqueous NaCl solution, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by the silica gel column chromatography to obtain the title compound.

Workup

  1. temperatureunder cooling with ice
  2. temperaturewere heated
  3. temperatureunder reflux for 2 hours
  4. customThe solvent was evaporated
  5. customThe reaction liquid
  6. extractionAfter the extraction with dichloromethane
  7. washthe organic layer was successively washed with saturated aqueous sodium hydrogencarbonate solution and saturated aqueous NaCl solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe solvent was evaporated
  10. customthe residue was purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-a188eb4a90d0445e998d98b4356b3a26
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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