N-Methylphenylalanine → Boc-N-Me-Phe-OH

HRID 1903870Notes

Reaction equation

HRID 1903870 reaction equation
[NH:1]([CH3:13])[C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(O[C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])(C)(C)C>C(O)(C)(C)C.[OH-].[Na+].O>[C:19]([N:1]([CH3:13])[C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:25]

Participants

6

Reactant 2

HCID 6951135N-MethylphenylalanineHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

Product 1

HCID 7010602Boc-N-Me-Phe-OH

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

3.6 g of H-MePhe-OH are dissolved in a mixture of tert.-butanol, 25 ml of 10% aqueous KHCO3 solution and 5 ml of 4 N sodium hydroxide. 8 ml of di-tert.-butylcarbonate are added and the mixture stirred for 2 days at room temperature. The reaction mixture is diluted with ca. 100 ml of water and extracted with ether. The aqueous phase is acidified, with stirring to pH 2. The precipitated product is extracted with acetic acid, the extract washed with water and dried over Na2SO4. The liquid is evaporated and the product crystallised from ether/petroleum ether to yield Boc-MePhe-OH. M.P. 87°.

Workup

  1. extractionextracted with ether
  2. stirringwith stirring to pH 2
  3. extractionThe precipitated product is extracted with acetic acid
  4. washthe extract washed with water
  5. dry with materialdried over Na2SO4
  6. customThe liquid is evaporated
  7. customthe product crystallised from ether/petroleum ether

Sources & evidence

ORD record
ord-fe10ff17bbca40a7bfd30a46f589f898
Source dataset
uspto-grants-1984_03
Patent number
US04438103

Reaction notes

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