Water → tert-butyl N-[3-(tert-butoxycarbonyl)benzyl]-L-phenylalaninate

HRID 1497510Notes

Reaction equation

HRID 1497510 reaction equation
Cl.[NH2:2][C@H:3]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][C:26]1[CH:27]=[C:28]([CH:36]=[CH:37][CH:38]=1)[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30].O>C(#N)C>[C:32]([O:31][C:29]([C:28]1[CH:27]=[C:26]([CH:38]=[CH:37][CH:36]=1)[CH2:25][NH:2][C@H:3]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:30])([CH3:35])([CH3:33])[CH3:34]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 11459563L-Phenylalanine, 1,1-dimethylethyl ester, hydrochloride (1:1)HCID 14591193tert-Butyl 3-(bromomethyl)benzoate

Product 1

HCID 90281993tert-butyl N-[3-(tert-butoxycarbonyl)benzyl]-L-phenylalaninateYield 56%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of tert-butyl L-phenylalaninate hydrochloride (456 mg) in acetonitrile (8.00 mL) were added potassium carbonate (510 mg) and tert-butyl 3-(bromomethyl)benzoate (400 mg), followed by stirring at room temperature overnight. To the reaction suspension was added water, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain tert-butyl N-[3-(tert-butoxycarbonyl)benzyl]-L-phenylalaninate (340 mg).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-9bfdf9591b0c403ca46125473738b479
Source dataset
uspto-grants-2015_12
Patent number
US09199927B2

Reaction notes

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