Methanol → 3-Iodo-α-methyl-D-phenylalanine methyl ester

HRID 857119Notes

Reaction equation

HRID 857119 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][CH:14]=1)[CH2:5][C@:6]([CH3:11])([C:8]([OH:10])=[O:9])[NH2:7].S(Cl)(Cl)=O.[CH3:19]O>>[I:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][CH:14]=1)[CH2:5][C@:6]([CH3:11])([C:8]([O:10][CH3:19])=[O:9])[NH2:7]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 10357711H-alpha-Me-D-Phe(3-I)-OH

Product 1

HCID 693445153-Iodo-α-methyl-D-phenylalanine methyl ester

Procedure

A solution of 3-iodo-α-methyl-D-phenylalanine (0.9 g) in MeOH (50 ml) was treated with thionyl chloride (3.5 ml) and the mixture was heated to reflux for 3 days. The solvent was removed under reduced pressure and the residue was dissolved in EtOAc and washed with aqueous sodium bicarbonate, brine, dried (MgSO4) and evaporated to dryness to give the title compound (0.73 g) LCMS RT=2.12 min.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 3 days
  3. customThe solvent was removed under reduced pressure
  4. dissolutionthe residue was dissolved in EtOAc
  5. washwashed with aqueous sodium bicarbonate, brine
  6. dry with materialdried (MgSO4)
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-2645e9c24a324bbf91119a7507b19592
Source dataset
uspto-grants-2006_12
Patent number
US07144908B2

Reaction notes

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