Hydrochloric Acid → O-[4-(4-hydroxyphenoxy)benzyl]-3,5-diiodo-L-tyrosine
Reaction equation
O.[OH-].[Li+].C[O:5][C:6](=[O:40])[C@H:7]([CH2:15][C:16]1[CH:21]=[C:20]([I:22])[C:19]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][C:32]3[CH:37]=[CH:36][C:35]([OH:38])=[CH:34][CH:33]=3)=[CH:27][CH:26]=2)=[C:18]([I:39])[CH:17]=1)[NH:8]C(=O)C(F)(F)F.Cl>O1CCCC1.O>[OH:38][C:35]1[CH:34]=[CH:33][C:32]([O:31][C:28]2[CH:29]=[CH:30][C:25]([CH2:24][O:23][C:19]3[C:18]([I:39])=[CH:17][C:16]([CH2:15][C@@H:7]([C:6]([OH:40])=[O:5])[NH2:8])=[CH:21][C:20]=3[I:22])=[CH:26][CH:27]=2)=[CH:37][CH:36]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
Lithium hydroxide monohydrate (47 mg, 1.12 mmol) was added to a solution of N-trifluoroacetyl-O-[4-(4-hydroxy-phenoxy)benzyl]-3,5-diiodo-L-tyrosine methyl ester (235 mg, 0.317 mmol) in tetrahydrofuran (2 ml)-water (1 ml) under ice cooling and the mixture was reacted at room temperature for 7.5 hrs., and then at 0-5° C. for 16 hrs. The reaction mixture was diluted with water, adjusted to pH 4-5 under ice cooling with 1N hydrochloric acid (0.79 ml) and stirred at room temperature for 1.5 hrs. The precipitates were collected by filtration, washed with water and ethanol in turn and dried to give O-[4-(4-hydroxyphenoxy)benzyl]-3,5-diiodo-L-tyrosine (188 mg, 90%) as pale yellow crystals.
Workup
- customthe mixture was reacted at room temperature for 7.5 hrs
- filtrationThe precipitates were collected by filtration
- washwashed with water and ethanol in turn
- customdried
Sources & evidence
- ORD record
- ord-12fe58cc432e4d7a8fc26d15ae58bb9a
- Source dataset
- uspto-grants-2008_03
- Patent number
- US07345068B2
Reaction notes
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