Potassium thiocyanate → (-)-alpha-Amino-3-(thiocyanatomethyl)-4-hydroxybenzeneacetic acid

HRID 225312Notes

Reaction equation

HRID 225312 reaction equation
[NH2:1][CH:2]([C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]([CH2:13]Cl)[CH:7]=1)[C:3]([OH:5])=[O:4].[S-:15][C:16]#[N:17].[K+]>CO>[NH2:1][CH:2]([C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]([CH2:13][S:15][C:16]#[N:17])[CH:7]=1)[C:3]([OH:5])=[O:4]

Participants

4

Reactant 2

HCID 516872Potassium thiocyanateHCID 20296136(-)-alpha-Amino-3-(chloromethyl)-4-hydroxybenzeneacetic acid

Product 1

HCID 23329809(-)-alpha-Amino-3-(thiocyanatomethyl)-4-hydroxybenzeneacetic acidYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (-)-α-amino-3-(chloromethyl)-4-hydroxybenzeneacetic acid (0.5 g, 1.98 mmole) and potassium thiocyanate (0.4 g, 4.12 mmole) in 10 ml of methanol is stirred at room temperature for 16 hours. The reaction mixture is filtered to remove the potassium chloride, the filtrate is evaporated and to the residue is added saturated aqueous sodium bicarbonate until the pH is 7. The title compound precipitates as a white powder which is filtered and dried. (1.83 g, 78% yield), NMR (TFA-D+D2O) ppm (δ) 4.1 (s,2), 5.08 (s,1), 6.9-7.3 (m,3).

Workup

  1. filtrationThe reaction mixture is filtered
  2. customto remove the potassium chloride
  3. customthe filtrate is evaporated and to the residue
  4. additionis added saturated aqueous sodium bicarbonate until the pH is 7
  5. customThe title compound precipitates as a white powder which
  6. filtrationis filtered
  7. customdried

Sources & evidence

ORD record
ord-7a45f95689624c58861869abfc3cb15a
Source dataset
uspto-grants-1980_11
Patent number
US04236002

Reaction notes

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