Methanol → Methyl 3-Amino-3-(4-hydroxyphenyl)propanoate

HRID 526316Notes

Reaction equation

HRID 526316 reaction equation
[NH2:1][CH:2]([C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)[CH2:3][C:4]([OH:6])=[O:5].S(Cl)(Cl)=O.[CH3:18]O>>[CH3:18][O:5][C:4](=[O:6])[CH2:3][CH:2]([NH2:1])[C:7]1[CH:8]=[CH:9][C:10]([OH:13])=[CH:11][CH:12]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 4403113-Amino-3-(4-hydroxyphenyl)propanoic acid

Product 1

HCID 58961718Methyl 3-Amino-3-(4-hydroxyphenyl)propanoateYield 80%

Conditions

Temperature
0 °C

Procedure

5.298 g (29.24 mmol) commercial 3-amino-3-(4-hydroxyphenyl)propionic acid were suspended in 136 ml methanol, the mixture cooled to 0° C. and 3.20 ml (43.86 mmol) thionyl chloride were slowly added. The mixture was stirred at room temperature for 20 hours and concentrated. The residue was treated with saturated sodium hydrogen carbonate solution and extracted with dichloromethane and dichloromethane/2-propanol 8:2. The organic part was concentrated to give 5.09 g (80%) 3-amino-3-(4-hydroxyphenyl)propionic acid methyl ester.

Workup

  1. concentrationconcentrated
  2. additionThe residue was treated with saturated sodium hydrogen carbonate solution
  3. extractionextracted with dichloromethane and dichloromethane/2-propanol 8:2
  4. concentrationThe organic part was concentrated

Sources & evidence

ORD record
ord-7cd9ddb96d9a4d888d87eb6794335731
Source dataset
uspto-grants-2016_05
Patent number
US09345793B2

Reaction notes

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