Hydrochloric Acid → HCID 9855818, compound

HRID 983692Notes

Reaction equation

HRID 983692 reaction equation
C[O:2][C:3](=[O:17])[CH2:4][C@:5]1([CH2:11][NH:12]C(OC)=O)[CH2:9][CH2:8][C@@H:7]([CH3:10])[CH2:6]1.[ClH:18]>O1CCOCC1.O>[ClH:18].[NH2:12][CH2:11][C@@:5]1([CH2:4][C:3]([OH:17])=[O:2])[CH2:9][CH2:8][C@@H:7]([CH3:10])[CH2:6]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 9856229HCID 9856229, compound

Product 1

HCID 9855818HCID 9855818, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

[(1S,3R)-1-(Methoxycarbonylamino-methyl)-3-methyl-cyclopentyl]-acetic acid methyl ester (2.84 g, 11.7 mmol) was refluxed in a mixture of 1,4-dioxane (15 mL) and 6N Hydrochloric acid (30 mL) for 17 hours. The mixture was allowed to cool, diluted with water (200 mL), and washed with dichloromethane (2×100 mL). The aqueous layer was evaporated under reduced pressure, and the residue was recrystallized from ethyl acetate/methanol (95:5) to give 1.28 g (53%) of ((1S,3R)-1-aminomethyl-3-methyl-cyclopentyl)-acetic acid hydrochloride;

Workup

  1. temperatureto cool
  2. washwashed with dichloromethane (2×100 mL)
  3. customThe aqueous layer was evaporated under reduced pressure
  4. customthe residue was recrystallized from ethyl acetate/methanol (95:5)

Sources & evidence

ORD record
ord-198fa236f6f542fba39e5134d5cf9cb5
Source dataset
uspto-grants-2005_03
Patent number
US06864390B2

Reaction notes

Loading…