Hydrazine hydrate (1:1) → 2-Aminooxy-3-phenyl-propionic acid benzyl ester

HRID 732861Notes

Reaction equation

HRID 732861 reaction equation
[CH2:1]([O:8][C:9](=[O:30])[CH:10]([O:18][N:19]1C(=O)C2C(=CC=CC=2)C1=O)[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.NN>CCO.CCOC(C)=O>[CH2:1]([O:8][C:9](=[O:30])[CH:10]([O:18][NH2:19])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 689612812-(1,3-Dioxo-1,3-dihydro-isoindol-2-yloxy)-3-phenyl-propionic acid benzyl ester

Product 1

HCID 689601412-Aminooxy-3-phenyl-propionic acid benzyl esterYield 80%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the compound from Step 6b (10.00 g, 24.94 mmol) in EtOH (150 mL) was added hydrazine monohydrate (2.50 mL, 49.88 mmol) at room temperature. The resulting mixture was stirred for 1 hour at room temperature, diluted with EtOAc (450 mL), washed with saturated NaHCO3, water (300 mL×2) and brine, dried (Na2SO4), filtered and concentrated to afford 6.73 g of crude product, which was purified by flash chromatography (silica gel, CH2Cl2/Hexane=15/1) to provide 5.37 g (80%) of the title compound. 13C NMR (CDCl3): δ171.9, 136.6, 135.4, 129.3, 129.2, 129.1, 128.4, 128.3, 128.2, 128.1, 128.0, 126.6, 83.8, 66.4, 37.3. Step 6d. Preparation of: N-Boc-2-Aminooxy-3-phenyl-propionic acid benzyl ester

Workup

  1. washwashed with saturated NaHCO3, water (300 mL×2) and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto afford 6.73 g of crude product, which
  6. customwas purified by flash chromatography (silica gel, CH2Cl2/Hexane=15/1)

Sources & evidence

ORD record
ord-47aa6366f4a643d293aba0d153dc34b3
Source dataset
uspto-grants-2009_09
Patent number
US07589067B2

Reaction notes

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