Potassium Hydroxide → 2-(6-[N,N-bis(tert-butoxycarbonyl)amino]-5-methyl-pyridin-3-ylmethyl)-malonic acid monoethyl ester

HRID 1789829Notes

Reaction equation

HRID 1789829 reaction equation
[OH-].[K+].[CH2:3]([O:5][C:6](=[O:36])[CH:7]([CH2:13][C:14]1[CH:15]=[N:16][C:17]([N:21]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[C:18]([CH3:20])[CH:19]=1)[C:8]([O:10]CC)=[O:9])[CH3:4]>C(O)C.C(Cl)Cl>[CH2:3]([O:5][C:6](=[O:36])[CH:7]([CH2:13][C:14]1[CH:15]=[N:16][C:17]([N:21]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:29]([O:31][C:32]([CH3:33])([CH3:34])[CH3:35])=[O:30])=[C:18]([CH3:20])[CH:19]=1)[C:8]([OH:10])=[O:9])[CH3:4]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 696502782-(6-[N,N-bis(tert-butoxycarbonyl)amino]-5-methyl-pyridin-3-ylmethyl)-malonic acid diethyl ester

Product 1

HCID 538649462-(6-[N,N-bis(tert-butoxycarbonyl)amino]-5-methyl-pyridin-3-ylmethyl)-malonic acid monoethyl esterYield 88.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of KOH (154 mg, 2.75 mmol) in ethanol (2 mL) was added to a solution 2-(6-[N,N-bis(tert-butoxycarbonyl)amino]-5-methyl-pyridin-3-ylmethyl)-malonic acid diethyl ester (1.2 g, 2.50 mmol) in ethanol (10 mL) and methylene chloride (4 mL) at 0° C. The mixture was stirred for 18 h at room temperature. The mixture was concentrated under reduced pressure and the residue dissolved in water. Ethyl acetate was added and the organic layer was washed with 0.5 M HCl, water, brine and dried. After filtration and concentration under reduced pressure gave crude 2-(6-[N,N-bis(tert-butoxy-carbonyl)amino]-5-methyl-pyridin-3-ylmethyl)-malonic acid monoethyl ester (1.0 g, 88%).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutionthe residue dissolved in water
  3. additionEthyl acetate was added
  4. washthe organic layer was washed with 0.5 M HCl, water, brine
  5. customdried
  6. filtrationAfter filtration and concentration under reduced pressure

Sources & evidence

ORD record
ord-e3ec7f046bc24f2f8fdc07ad0f018346
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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