Sodium Nitrite → HCID 53755901, compound

HRID 439579Notes

Reaction equation

HRID 439579 reaction equation
[ClH:1].[CH3:2][O:3][C:4]1[CH:15]=[CH:14][C:7]([CH2:8][C@@H:9]([C:11]([OH:13])=[O:12])N)=[CH:6][C:5]=1[N+:16]([O-:18])=[O:17].N([O-])=O.[Na+]>C(OCC)(=O)C>[Cl:1][C@@H:9]([CH2:8][C:7]1[CH:14]=[CH:15][C:4]([O:3][CH3:2])=[C:5]([N+:16]([O-:18])=[O:17])[CH:6]=1)[C:11]([OH:13])=[O:12]

Participants

4

Reactant 2

HCID 23668193Sodium NitriteHCID 70114073HCID 70114073, compound

Product 1

HCID 53755901HCID 53755901, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To suspension solution of O-methyl-3-nitro-L-tyrosine.hydrochloride(4.93 g) in 6N aqueous hydrochloric acidwas added under ice-cooling, sodium nitrite (1.97 g) and was stirredat the same temperature for 1 and 1/2 hour and further at roomtemperature for 3 hours. The resultant suspension solution wasextracted with ethyl acetate (50 ml×3). After the ethyl acetate layerwas washed with saturated brine, dried over anhydrous sodiumsulfate. The solvent was evaporated in vacuo to give (S)-2-chloro-3-(4-methoxy-3-nitrophenyl)propionicacid (4.46 g).

Workup

  1. temperaturecooling
  2. customfor 1 and 1/2 hour
  3. washAfter the ethyl acetate layerwas washed with saturated brine
  4. dry with materialdried over anhydrous sodiumsulfate
  5. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-1321a55eaec74c7d8e61c68a94265892
Source dataset
uspto-grants-1996_05
Patent number
US05514773

Reaction notes

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