Hydrochloric Acid → HCID 67232787, compound

HRID 964616Notes

Reaction equation

HRID 964616 reaction equation
Cl.Cl.[NH2:3][C@@:4]([CH3:16])([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)[C:5]([OH:7])=[O:6].[CH3:17][CH2:18]O>>[NH2:3][C@@:4]([CH3:16])([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)[C:5]([O:7][CH2:17][CH3:18])=[O:6]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 131720725HCID 131720725, compound

Product 1

HCID 67232787HCID 67232787, compoundYield 91%

Conditions

Temperature
20 °C

Procedure

HCl gas was bubbled through a solution of (S)-α-amino-4-methoxy-α-methyl-benzeneacetic acid, hydrochloride salt (2.0 g, 8.6 mmol) in EtOH (25 mL) at 4° C. The solution was stirred for 1 hour at 20° C. before being refluxed for 5 hours. After cooling, the solution was concentrated in vacuo. The resulting oil was dissolved in CH2Cl2, and washed with aq. NaHCO3 ; the aqueous phase was back-extracted with CH2Cl2. The combined organic fractions were washed with H2O, brine and dried over Na2SO4 prior to concentration to yield the title compound as a yellow oil (1.75 g, 91%).

Workup

  1. temperaturebefore being refluxed for 5 hours
  2. temperatureAfter cooling
  3. concentrationthe solution was concentrated in vacuo
  4. dissolutionThe resulting oil was dissolved in CH2Cl2
  5. washwashed with aq. NaHCO3
  6. extractionthe aqueous phase was back-extracted with CH2Cl2
  7. washThe combined organic fractions were washed with H2O, brine
  8. dry with materialdried over Na2SO4
  9. concentrationto concentration

Sources & evidence

ORD record
ord-55a499e523164afc93cadda2f9b259ed
Source dataset
uspto-grants-1998_06
Patent number
US05770615

Reaction notes

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