L-Tyrosine 1,1-dimethylethyl ester → N-(4-ethoxy-1-oxo-1,2,5-thiadiazol-3-yl)-L-tyrosine tert-butyl ester

HRID 1070447Notes

Reaction equation

HRID 1070447 reaction equation
C(O[C:4]1[C:8]([O:9][CH2:10][CH3:11])=[N:7][S:6](=[O:12])[N:5]=1)C.[C:13]([O:17][C:18](=[O:29])[C@H:19]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1)[NH2:20])([CH3:16])([CH3:15])[CH3:14]>C(O)C>[C:13]([O:17][C:18](=[O:29])[C@H:19]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1)[NH:20][C:4]1[C:8]([O:9][CH2:10][CH3:11])=[N:7][S:6](=[O:12])[N:5]=1)([CH3:16])([CH3:14])[CH3:15]

Participants

4

Reactant 2

HCID 6950582L-Tyrosine 1,1-dimethylethyl esterHCID 12927269Diethoxy-1,2,5-thiadiazol-1-one

Product 1

HCID 53908618N-(4-ethoxy-1-oxo-1,2,5-thiadiazol-3-yl)-L-tyrosine tert-butyl esterYield 882.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3,4-diethoxy-1-oxo-1,2,5-thiadiazole (1 g, 0.52 mmol) and L-tyrosine t-butyl ester (1.25 g, 0.52 mmol) in ethanol (25 mL) was stirred at room temperature for 60 hr. Solvent was removed under reduced pressure and the residue purified by flash column chromatography (silica, hexane:EtOAc 1:1 to give N-(4-ethoxy-1-oxo-1,2,5-thiadiazol-3-yl)-L-tyrosine tert-butyl ester (1.75 g, 88%). MS (+ESI, m/e) 382 (M+H)+.

Workup

  1. customSolvent was removed under reduced pressure
  2. customthe residue purified by flash column chromatography (silica, hexane:EtOAc 1:1

Sources & evidence

ORD record
ord-6e465b4d01ac48978b3b77c5bbca7f73
Source dataset
uspto-grants-2005_06
Patent number
US06903088B2

Reaction notes

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