Water → O-benzyl-N-((tert-butoxy)carbonyl)-L-tyrosine

HRID 1351762Notes

Reaction equation

HRID 1351762 reaction equation
[C:1]([NH:8][C@H:9]([C:18]([OH:20])=[O:19])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C[O-].[Na+].CO.[CH2:26](Cl)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.O>CO.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:1]([NH:8][C@H:9]([C:18]([OH:20])=[O:19])[CH2:10][C:11]1[CH:12]=[CH:13][C:14]([O:17][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:15][CH:16]=1)([O:3][C:4]([CH3:5])([CH3:7])[CH3:6])=[O:2]

Participants

7

Reactant 4

HCID 962WaterHCID 7503Benzyl ChlorideHCID 117439L-Tyrosine, N-(1,1-dimethylethoxy)carbonyl-HCID 23694274Sodium methanolate methanol

Product 1

HCID 98763O-benzyl-N-((tert-butoxy)carbonyl)-L-tyrosineYield 84%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of N-Boc-tyrosine (281 mg, 1.0 mmol) in methanol (0.5 mL) were added 28% sodium methoxide-methanol solution (0.42 mL, 2.1 mmol), benzyl chloride (115 μL, 1.4 mmol) and tetrabutylammonium iodide (28 mg) and the mixture was stirred at 40° C. for 24 hr. Then, water (2 mL) was added to make the system homogeneous, which system was then analyzed by HPLC (conversion yield 89%). The aqueous solution was washed with toluene (0.5 mL), neutralized with hydrochloric acid to allow precipitation of a solid, and the solid was filtered and dried to give the objective N-Boc-(O-benzyl)tyrosine (312 mg, yield 84%).

Workup

  1. washThe aqueous solution was washed with toluene (0.5 mL)
  2. customprecipitation of a solid
  3. filtrationthe solid was filtered
  4. customdried

Sources & evidence

ORD record
ord-902e33798fa1413080ba7e217beb510f
Source dataset
uspto-grants-2007_05
Patent number
US07217835B2

Reaction notes

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