Methanol → Methyl 3-iodo-alpha-methyl-D-phenylalaninate

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

Reactant 3

HCID 887Methanol

HCID 24386Thionyl Chloride

HCID 10357711H-alpha-Me-D-Phe(3-I)-OH

Product 1

HCID 69344515Methyl 3-iodo-alpha-methyl-D-phenylalaninate

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.