O-Benzylhydroxylamine → HCID 13242803, compound

HRID 1016611Notes

Reaction equation

HRID 1016611 reaction equation
[CH2:1]([C:8](=[CH2:12])[C:9]([OH:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:13]([O:20][NH2:21])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(OCC)C>[CH2:1]([CH:8]([CH2:12][NH:21][O:20][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:9]([OH:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 102313O-BenzylhydroxylamineHCID 3035712-Benzylacrylic Acid

Product 1

HCID 13242803HCID 13242803, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-benzyl-acrylic acid (8.0 g, 55 mmol) and O-benzylhydroxylamine (16.0 g, 130 mmol) was heated at 80° C. for 18 hours. The reaction mixture was cooled, diluted with diethyl ether (100 mL) and extracted with 1M sodium carbonate (3×100 mL). The combined aqueous extracts were acidified with 3M citric acid and then re-extracted with dichloromethane (3×100 mL). The combined organic extracts were washed with brine, dried over magnesium sulphate, filtered and concentrated under reduced pressure to yield 2-(R,S)-benzyl-3-benzyloxyamino-propionic acid as a white crystalline solid (7.82 g, 53%). 1H-NMR; δ (CDCl3), 7.61-7.15 (10H, m), 4.66 (2H, d, J=1.7 Hz), 3.13-2.94 (4H, m), 2.84-2.74 (1H, m).

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with 1M sodium carbonate (3×100 mL)
  3. extractionre-extracted with dichloromethane (3×100 mL)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-29988aa0debb454db7ccbebd1074bf96
Source dataset
uspto-grants-2002_11
Patent number
US06476067B1

Reaction notes

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