Acetic Acid → HCID 39237242, compound

HRID 2414380Notes

Reaction equation

HRID 2414380 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][C@@H:9](N)[C:10]([OH:12])=[O:11])[CH:3]=1.Cl.C(O)(=[O:17])C.N([O-])=O.[Na+]>C([O-])(=O)C.[Na+].O>[OH:17][C@H:9]([CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[CH:3]=1)[C:10]([OH:12])=[O:11]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 69936503-Methyl-D-phenylalanineHCID 23668193Sodium Nitrite

Product 1

HCID 39237242HCID 39237242, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 517045Sodium AcetateSolvent

Procedure

To a solution of D-3-methylphenylalanine.HCl (5.5 g, 25.5 mmol) and acetic acid (13.0 mL) in 0.04 M aqueous sodium acetate (750 mL) is added a solution of sodium nitrite (5.28 g, 76.5 mmol) in water (12.5 mL) dropwise, over 30 min, and the solution is allowed to stir for 3 h. This solution is then saturated with NaCl, and extracted with EtOAc (3×150 mL). The combined organic layers are washed with brine (3×150 mL), dried (MgSO4) and evaporated to yield (R)-2-hydroxy-3-(3-methylphenyl)-propionic acid.

Workup

  1. extractionsaturated with NaCl, and extracted with EtOAc (3×150 mL)
  2. washThe combined organic layers are washed with brine (3×150 mL)
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-0e91fab21d904e3ea59c9cf4d453a0ad
Source dataset
uspto-grants-2004_11
Patent number
US06812237B2

Reaction notes

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