Ammonia → Methyl 2-amino-2-(4-hydroxyphenyl)propionate

HRID 1919783Notes

Reaction equation

HRID 1919783 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](Br)([CH3:16])[C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=1)(=O)C.C1COCC1.[NH3:23]>C(O)C>[NH2:23][C:11]([C:8]1[CH:9]=[CH:10][C:5]([OH:4])=[CH:6][CH:7]=1)([CH3:16])[C:12]([O:14][CH3:15])=[O:13]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 8028TetrahydrofuranHCID 59235280Methyl 2-(4-acetoxyphenyl)-2-bromopropionate

Product 1

HCID 59235258Methyl 2-amino-2-(4-hydroxyphenyl)propionate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10 g of methyl 2-(4-acetoxyphenyl)-2-bromopropionate, 50 mL of THF and 30 mL of ethanol are introduced into a Woulff bottle at ambient temperature. The mixture is saturated with gaseous ammonia and stirred for one night at ambient temperature. The insoluble matter is filtered and purified over a silica column with 90/10 dichloromethane/methanol to yield the product (5 g; Yd=77%).

Workup

  1. filtrationThe insoluble matter is filtered
  2. custompurified over a silica column with 90/10 dichloromethane/methanol
  3. customto yield the product (5 g; Yd=77%)

Sources & evidence

ORD record
ord-b9d517dfee4d495194fecb5bf9fbcd19
Source dataset
uspto-grants-2012_05
Patent number
US08168667B2

Reaction notes

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