Hydrochloric Acid → 2-Amino-3-cyclooctylpropanoic acid

HRID 1018852Notes

Reaction equation

HRID 1018852 reaction equation
C([O:5][C:6](=[O:31])[CH:7]([N:17]=C(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:8][CH:9]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)(C)(C)C.Cl>CO.O>[NH2:17][CH:7]([CH2:8][CH:9]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)[C:6]([OH:31])=[O:5]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 865854002-(Benzhydrylidene-amino)-3-cyclooctyl-propionic acid tert-butyl ester

Product 1

HCID 184021902-Amino-3-cyclooctylpropanoic acidYield 62.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2-(Benzhydrylidene-amino)-3-cyclooctyl-propionic acid tert-butyl ester (2.00 g) in methanol (15 mL) was added 10N HCl solution (30 mL) and the mixture heated to reflux. After 20 h, the mixture was allowed to cool to room temperature, diluted with 20 mL of water, transferred to a separatory funnel and washed with ethyl acetate. The aqueous layer was then neutralized with 10N sodium hydroxide solution and further cooled to 0° C. The white solid was filtered off and air dried to give 590 mg of 2-Amino-3-cyclooctyl-propionic acid.

Workup

  1. temperaturethe mixture heated to reflux
  2. customtransferred to a separatory funnel
  3. washwashed with ethyl acetate
  4. temperaturefurther cooled to 0° C
  5. filtrationThe white solid was filtered off
  6. customair dried

Sources & evidence

ORD record
ord-cc013cc989034414829e764675829ac3
Source dataset
uspto-grants-2002_11
Patent number
US06482951B2

Reaction notes

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