Triethylamine → N-Boc-4-hydroxy-D-homophenylalanine

HRID 1902159Notes

Reaction equation

HRID 1902159 reaction equation
Br.[OH:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C@@H:11]([NH2:15])[C:12]([OH:14])=[O:13])=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:23]([O:27][C:28](ON=C(C1C=CC=CC=1)C#N)=[O:29])([CH3:26])([CH3:25])[CH3:24]>O1CCOCC1.O.C(OCC)(=O)C>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][C@@H:11]([NH:15][C:28]([O:27][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:29])[C:12]([OH:14])=[O:13])=[CH:7][CH:8]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrileHCID 56777052(R)-2-Amino-4-(4-hydroxyphenyl)butanoic acid hydrobromide

Product 1

HCID 53715645N-Boc-4-hydroxy-D-homophenylalanine

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a stirred solution of (2R)-4-(4-hydroxyphenyl)-2-amino-butanoic acid hydrobromide (5.0 g, 18.18 mmol) and triethylamine (5.25 mL, 2 eq) in dioxane (50 mL) and water (50 mL) at 0° C. was added a solution of 2-(tert-butoxycarbonyloxyimino)-2-phenylacetonitile (BOCON) (4.9 g) in dioxane (10 mL). The reaction mixture was allowed to warm up to room temperature and stirred for five hours when it became homogeneous: The reaction mixture was diluted with ethyl acetate (EtOAc) and the organic was seperated. The aqueous layer was acidified with citric acid (20%) and extracted with EtOAc. The combined organics were washed with brine, dried over magnesium sulfate, filtered and evaporated to give the desired material.

Workup

  1. customthe organic was seperated
  2. extractionextracted with EtOAc
  3. washThe combined organics were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-9505eb161b29492f841f33e095aba981
Source dataset
uspto-grants-1996_11
Patent number
US05578593

Reaction notes

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