Sodium Iodide → Tyrosine Methyl Ester

HRID 2298257Notes

Reaction equation

HRID 2298257 reaction equation
[CH3:1][O:2][C:3](=[O:31])[C@H:4]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=1)[NH:5]C(=O)[C@@H]1CCCN1S(C1C=CC(C)=CC=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CC(=O)CC>[CH3:1][O:2][C:3](=[O:31])[C@H:4]([CH2:23][C:24]1[CH:25]=[CH:26][C:27]([OH:30])=[CH:28][CH:29]=1)[NH2:5]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 54334627HCID 54334627, compound

Product 1

HCID 70652Tyrosine Methyl Ester

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

N-(Toluene-4-sulfonyl)-L-prolyl-O-[(1-tert-butoxycarbonyl)-piperidin-3-yl)methyl]-L-tyrosine methyl ester was prepared via O-alkylation of N-(toluene-4-sulfonyl)-L-prolyl-L-tyrosine methyl ester with N-Boc-3-piperidinemethyl tosylate in refluxing 2-butanone in the presence of potassium carbonate and sodium iodide to provide a solid, mp=60-62° C.

Workup

  1. customto provide a solid, mp=60-62° C.

Sources & evidence

ORD record
ord-c98bd1b439a64588b72bb41151ed72d6
Source dataset
uspto-grants-2002_12
Patent number
US06492421B1

Reaction notes

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