Potassium Hydroxide → HCID 67167194, compound

HRID 1808803Notes

Reaction equation

HRID 1808803 reaction equation
[OH-].[K+].[CH:3]1([CH:8]([NH:14][C:15]([O:17][CH3:18])=[O:16])[C:9]([O:11]CC)=[O:10])[CH2:7][CH2:6][CH2:5][CH2:4]1>O.C(O)C>[CH:3]1([CH:8]([NH:14][C:15]([O:17][CH3:18])=[O:16])[C:9]([OH:11])=[O:10])[CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 67772933HCID 67772933, compound

Product 1

HCID 67167194HCID 67167194, compoundYield 89.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

KOH (3.87 g, 69.0 mmol) in water (50 mL) was added to ethyl 2-cyclopentyl-2-(methoxycarbonylamino)acetate (Compound I2.1) (7.6 g, 33.2 mmol) in ethanol (20 mL). The resultant mixture was stirred at rt for 5 h. Part of the solvent was removed under reduce pressure. The remaining mixture was extracted with Et2O (2×50 mL). The pH of the water layer was acidified by additions of HCl (1N, 20 mL) and the resultant mixture was extracted with DCM (3×50 mL), dried (MgSO4) and concentrated under reduce pressure. The residue was purified via Biotage (gradient: 10-80% of DCM/MeOH/HOAc (1: 0.05: 0.01) in DCM, KP-SIL 340 g column), KP-SIL 340 g column) to give the title product (5.95 g, 85%). 1H NMR (600 MHz, CDCl3) 1.26-1.48, 1.49-1.68, 1.68-1.85, 2.28, 3.69, 4.31, 5.12. Total no of protons: 14.

Workup

  1. customPart of the solvent was removed
  2. extractionThe remaining mixture was extracted with Et2O (2×50 mL)
  3. extractionthe resultant mixture was extracted with DCM (3×50 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified via Biotage (gradient: 10-80% of DCM/MeOH/HOAc (1: 0.05: 0.01) in DCM, KP-SIL 340 g column), KP-SIL 340 g column)

Sources & evidence

ORD record
ord-5555e72195154f438eaee0025eb93dca
Source dataset
uspto-grants-2013_01
Patent number
US08361998B2

Reaction notes

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