Triethylamine → tert-butyl (2S)-2-amino-3-phenylpropanoate

HRID 1367688Notes

Reaction equation

HRID 1367688 reaction equation
Cl.[C:2]([O:6][C:7](=[O:17])[C@H:8]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[NH2:9])([CH3:5])([CH3:4])[CH3:3].C(N(CC)CC)C>O1CCCC1>[C:2]([O:6][C:7](=[O:17])[C@H:8]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[NH2:9])([CH3:5])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 11459563L-Phenylalanine, 1,1-dimethylethyl ester, hydrochloride (1:1)

Product 1

HCID 6931633tert-butyl (2S)-2-amino-3-phenylpropanoateYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into a round-bottom flask having a capacity of 25 mL were introduced 257 mg (1 mmol) of phenylalanine t-butyl ester hydrochloride and 10 mL of tetrahydrofuran. To the resultant solution was added 101 mg (1 mmol) of triethylamine. The mixture was stirred at room temperature for 1 hour. This reaction mixture was filtered through a syringe filter to obtain a tetrahydrofuran solution of phenylalanine t-butyl ester. To this solution was added 304 mg (1 mmol) of bis(4-nitrophenyl) carbonate. The mixture was stirred at room temperature for 3 hours. This reaction mixture was analyzed by NMR spectroscopy using dioxane as an internal reference. As a result, it was found that N-(4-nitrophenoxycarbonyl)phenylalanine t-butyl ester had been obtained in a yield of 97%. Furthermore, this reaction mixture was subjected to column isolation to obtain N-(4-nitrophenoxycarbonyl)phenylalanine t-butyl ester in an amount of 352 mg (isolation yield, 91%).

Workup

  1. customInto a round-bottom flask having
  2. filtrationThis reaction mixture was filtered through a syringe
  3. filtrationfilter

Sources & evidence

ORD record
ord-890b6867ad4d4d309b534f2507d50cf2
Source dataset
uspto-grants-2011_02
Patent number
US07893274B2

Reaction notes

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