Perchloric Acid → Tert-butyl 3-amino-3-(4-hydroxyphenyl)propanoate

HRID 526368Notes

Reaction equation

HRID 526368 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].Cl(O)(=O)(=O)=O>C(OC(C)(C)C)(=O)C>[C:7]([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)([CH3:12])([CH3:8])[CH3:2]

Participants

4

Reactant 2

HCID 24247Perchloric AcidHCID 4403113-Amino-3-(4-hydroxyphenyl)propanoic acid

Product 1

HCID 71258939Tert-butyl 3-amino-3-(4-hydroxyphenyl)propanoateYield 152.7%

Reagents, catalysts & solvents 1

HCID 10908tert-Butyl acetateSolvent

Conditions

Temperature
15 °C

Procedure

1.00 g (5.52 mmol) commercial 3-amino-3-(4-hydroxy-phenyl)-propionic acid were suspended in 20 ml tert-butyl acetate and the mixture cooled to 15° C. 0.90 ml (11.10 mmol) perchloric acid were slowly added and the mixture stirred at 20° C. for 1.5 hours. The solution was extracted with saturated sodium hydrogen carbonate solution. The aqueous layer was brought to pH=8 with sodium carbonate and extracted with ethyl acetate. The organic parts were combined, dried over sodium sulfate and concentrated to yield 1.0 g (60%) racemic 3-amino-3-(4-hydroxy-phenyl)-propionic acid tert-butyl ester. This was separated into the enantiomers by HPLC:

Workup

  1. extractionThe solution was extracted with saturated sodium hydrogen carbonate solution
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-40c4fc236bc243ec80fd29cc05197829
Source dataset
uspto-grants-2016_05
Patent number
US09345793B2

Reaction notes

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