Diethyl Ether → (R)-3-(3,4-diethyl-phenyl)-2-hydroxy-propionic acid

HRID 644347Notes

Reaction equation

HRID 644347 reaction equation
N([O-])=O.[Na+].N[C@H:6]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH3:18])=[C:13]([CH2:19][CH3:20])[CH:12]=1)[C:7]([OH:9])=[O:8].C([O:23]CC)C>O.OS(O)(=O)=O>[CH2:19]([C:13]1[CH:12]=[C:11]([CH2:10][C@@H:6]([OH:23])[C:7]([OH:9])=[O:8])[CH:16]=[CH:15][C:14]=1[CH2:17][CH3:18])[CH3:20]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 23668193Sodium NitriteHCID 45095428(2R)-2-Amino-3-(3,4-diethylphenyl)propanoic acid

Product 1

HCID 45095469(R)-3-(3,4-diethyl-phenyl)-2-hydroxy-propionic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

A solution of 3.2 g (47 mmol) sodium nitrite in 20 mL water was slowly added dropwise with stirring to an ice-cooled mixture of 2.0 g (7.8 mmol) (R)-2-amino-3-(3,4-diethyl-phenyl)-propionic acid in 60 mL 0.5 M H2SO4. The reaction mixture was stirred for 3 h while cooling with ice and for 3 days at RT, combined with 80 mL diethyl ether, vigorously stirred and the organic phase is separated off. The aqueous phase was again extracted with 80 mL diethyl ether, the combined organic phases were dried and evaporated down under reduced pressure. The residue was purified by chromatography on silica gel and the product fractions were evaporated down under reduced pressure.

Workup

  1. temperaturecooled
  2. stirringvigorously stirred
  3. customthe organic phase is separated off
  4. extractionThe aqueous phase was again extracted with 80 mL diethyl ether
  5. customthe combined organic phases were dried
  6. customevaporated down under reduced pressure
  7. customThe residue was purified by chromatography on silica gel
  8. customthe product fractions were evaporated down under reduced pressure

Sources & evidence

ORD record
ord-14ca285b582e46ad8fd3dcdf440cb2b0
Source dataset
uspto-grants-2010_04
Patent number
US07700589B2

Reaction notes

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