Hydrochloric Acid → 2-Amino-3-cycloheptylpropanoic acid

HRID 1018847Notes

Reaction equation

HRID 1018847 reaction equation
C([O:5][C:6](=[O:30])[CH:7]([N:16]=C(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:8][CH:9]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)(C)(C)C.Cl>CO>[NH2:16][CH:7]([CH2:8][CH:9]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)[C:6]([OH:30])=[O:5]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 865853992-(Benzhydrylidene-amino)-3-cycloheptyl-propionic acid tert-butyl ester

Product 1

HCID 221843862-Amino-3-cycloheptylpropanoic acidYield 53.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-(Benzhydrylidene-amino)-3-cycloheptyl-propionic acid tert-butyl ester (1.34 g; 3.31 mmol) in methanol (5 mL) was added 10N HCl solution (15 mL) and the mixture heated to reflux. After 15 h, the mixture was allowed to cool to room temperature and transferred to a separatory funnel and washed with ethyl acetate. The aqueous layer was then neutralized with concentrated ammonium hydroxide solution and the white solid was filtered off and air dried to give 329 mg of 2-Amino-3-cycloheptyl-propionic acid.

Workup

  1. temperaturethe mixture heated to reflux
  2. customtransferred to a separatory funnel
  3. washwashed with ethyl acetate
  4. filtrationthe white solid was filtered off
  5. customair dried

Sources & evidence

ORD record
ord-91989a8bdd7242319ae9b2738ae692c3
Source dataset
uspto-grants-2002_11
Patent number
US06482951B2

Reaction notes

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