Potassium Hydroxide → HCID 86594382, compound

HRID 902925Notes

Reaction equation

HRID 902925 reaction equation
C([O:3][C:4](=[O:22])[CH:5]([C:14](=[O:21])[NH:15][O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])C.[OH-].[K+]>C(O)C>[C:10]([O:9][C:7](=[O:8])[CH2:6][CH:5]([C:14](=[O:21])[NH:15][O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C:4]([OH:22])=[O:3])([CH3:13])([CH3:11])[CH3:12]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 86594383HCID 86594383, compound

Product 1

HCID 86594382HCID 86594382, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 2-tert-butoxycarbamoyl-succinic acid 4-tert-butyl ester 1-ethyl ester (5.92 g, 18.6 mmol) in ethanol (224 mL) was added 20.91 mL of a 10% aqueous solution of potassium hydroxide. The resulting mixture was then stirred at room temperature for 3 hours and then worked up. The crude product was purified by flash chromatography (SiO2, 90% dichloromethane-10% methanol) to afford 3.06 g (57.0% yield) of the desired mono acid: 1H NMR (CDCl3, 400 MHz) 3.65 (t, 1H), 2.78, (dd, 3H), 1.45 (s, 9H), 1.25s, 9H); 13C NMR (CDCl3, 400 MHz) 171.2, 169.7, 84.0, 82.0, 46.8, 34.5, 28.5, 26.5.

Workup

  1. customThe crude product was purified by flash chromatography (SiO2, 90% dichloromethane-10% methanol)
  2. customto afford 3.06 g (57.0% yield) of the desired mono acid
  3. custom1H NMR (CDCl3, 400 MHz) 3.65 (t, 1H), 2.78, (dd, 3H), 1.45 (s, 9H), 1.25s, 9H

Sources & evidence

ORD record
ord-c5fb61f200fc454583d3dc6fd498052d
Source dataset
uspto-grants-2008_04
Patent number
US07365091B2

Reaction notes

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