Triphenylphosphine → HCID 69316249, compound

HRID 1393365Notes

Reaction equation

HRID 1393365 reaction equation
CCOC(/N=N/C(OCC)=O)=O.[CH3:13][O:14][C:15](=[O:35])[C@H:16]([CH2:25][C:26]1[CH:31]=[C:30]([I:32])[C:29]([OH:33])=[C:28]([I:34])[CH:27]=1)[NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].[Br:36][CH2:37][CH2:38][CH2:39]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH3:13][O:14][C:15](=[O:35])[C@H:16]([CH2:25][C:26]1[CH:31]=[C:30]([I:32])[C:29]([O:33][CH2:39][CH2:38][CH2:37][Br:36])=[C:28]([I:34])[CH:27]=1)[NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:22])[CH3:23])=[O:19]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 123083-Bromo-1-propanolHCID 5462977Diethyl azodicarboxylateHCID 14753124HCID 14753124, compound

Product 1

HCID 69316249HCID 69316249, compoundYield 43.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethylazodicarboxylate (197 μ1, 1.25 mmol) was added dropwise to a solution of N-t-butoxycarbonyl-3,5-diiodo-L-tyrosine methyl ester (274 mg, 0.5 mmol), 3-bromo-1-propanol (76 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 0.5 hrs., at 0-5° C. for 0.5 hrs., and then at room temperature for 23 hrs. The solvent of the reaction mixture was distilled off at room temperature under reduced pressure. The residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=9) to give O-(3-bromopropyl)-N-t-butoxycarbonyl-3,5-diiodo-L-tyrosine methyl ester (145 mg, 43%) as colorless crystals.

Workup

  1. wait, at 0-5° C. for 0.5 hrs
  2. wait, and then at room temperature for 23 hrs
  3. distillationThe solvent of the reaction mixture was distilled off at room temperature under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=9)

Sources & evidence

ORD record
ord-a441bf279b59409cb2588bafb2332ad4
Source dataset
uspto-grants-2008_03
Patent number
US07345068B2

Reaction notes

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