Triphenylphosphine → N-trifluoroacetyl-O-[4-(4-hydroxy-phenoxy)benzyl]-3,5-diiodo-L-tyrosine methyl ester

HRID 1393367Notes

Reaction equation

HRID 1393367 reaction equation
CCOC(/N=N/C(OCC)=O)=O.[CH3:13][O:14][C:15](=[O:34])[C@H:16]([CH2:24][C:25]1[CH:30]=[C:29]([I:31])[C:28]([OH:32])=[C:27]([I:33])[CH:26]=1)[NH:17][C:18](=[O:23])[C:19]([F:22])([F:21])[F:20].[OH:35][C:36]1[CH:50]=[CH:49][C:39]([O:40][C:41]2[CH:48]=[CH:47][C:44]([CH2:45]O)=[CH:43][CH:42]=2)=[CH:38][CH:37]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH3:13][O:14][C:15](=[O:34])[C@H:16]([CH2:24][C:25]1[CH:26]=[C:27]([I:33])[C:28]([O:32][CH2:45][C:44]2[CH:47]=[CH:48][C:41]([O:40][C:39]3[CH:49]=[CH:50][C:36]([OH:35])=[CH:37][CH:38]=3)=[CH:42][CH:43]=2)=[C:29]([I:31])[CH:30]=1)[NH:17][C:18](=[O:23])[C:19]([F:22])([F:20])[F:21]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 13941953N-Trifluoroacetyl-3,5-diiodotyrosine methyl esterHCID 230339384-(4-Hydroxyphenoxy)benzylalcohol

Product 1

HCID 86598312N-trifluoroacetyl-O-[4-(4-hydroxy-phenoxy)benzyl]-3,5-diiodo-L-tyrosine methyl esterYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethylazodicarboxylate (40% toluene solution 0.55 ml) was added dropwise to a solution of N-trifluoroacetyl-3,5-diiodo-L-tyrosine methyl ester (272 mg, 0.5 mmol), 4-(4-hydroxyphenoxy)benzylalcohol (119 mg, 0.55 mmol) and triphenylphosphine (328 mg, 1.25 mmol) in tetrahydrofuran (5 ml) under argon atmosphere at −15° C., and the mixture was stirred at the same temperature for 1.5 hrs. The solvent of the reaction mixture was distilled off under reduced pressure. The residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=2) to give N-trifluoroacetyl-O-[4-(4-hydroxy-phenoxy)benzyl]-3,5-diiodo-L-tyrosine methyl ester (280 mg, 76%) as colorless crystals.

Workup

  1. distillationThe solvent of the reaction mixture was distilled off under reduced pressure
  2. customThe residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=2)

Sources & evidence

ORD record
ord-9ca0397011df4c128cadb1cfcad24497
Source dataset
uspto-grants-2008_03
Patent number
US07345068B2

Reaction notes

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