Ethyl Acetate → 2-(2-[N,N-bis(tert-butoxycarbonyl)amino]-pyrimidin-5-ylmethyl)-malonic acid monoethyl ester

HRID 1789869Notes

Reaction equation

HRID 1789869 reaction equation
[OH-].[K+].[CH2:3]([O:5][C:6](=[O:35])[CH:7]([CH2:13][C:14]1[CH:15]=[N:16][C:17]([N:20]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[N:18][CH:19]=1)[C:8]([O:10]CC)=[O:9])[CH3:4].CCOC(C)=O>CCO.CCO.C(Cl)Cl>[CH2:3]([O:5][C:6](=[O:35])[CH:7]([CH2:13][C:14]1[CH:15]=[N:16][C:17]([N:20]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:28]([O:30][C:31]([CH3:33])([CH3:34])[CH3:32])=[O:29])=[N:18][CH:19]=1)[C:8]([OH:10])=[O:9])[CH3:4]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 544517182-(2-[N,N-bis(tert-butoxycarbonyl)amino]-pyrimidin-5-ylmethyl)-malonic acid diethyl ester

Product 1

HCID 572694542-(2-[N,N-bis(tert-butoxycarbonyl)amino]-pyrimidin-5-ylmethyl)-malonic acid monoethyl esterYield 89.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 21584144Dichloromethane ethanolSolvent

Procedure

A solution of KOH (106 mg, 1.88 mmol) in EtOH (2 mL) was added to a solution of 2-(2-[N,N-bis(tert-butoxycarbonyl)amino]-pyrimidin-5-ylmethyl)-malonic acid diethyl ester (0.80 g, 1.71 mmol) in EtOH/methylene chloride (2:1, 12 mL) at 0° C. The mixture was stirred for 16 h at room temperature and EtOAc was added. The mixture was washed with 0.5 M HCl and brine, dried and concentrated under reduced pressure to give 2-(2-[N,N-bis(tert-butoxycarbonyl)amino]-pyrimidin-5-ylmethyl)-malonic acid monoethyl ester (0.67 g, 89%).

Workup

  1. washThe mixture was washed with 0.5 M HCl and brine
  2. customdried
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c0c425d244d24d478567e99075cddbd0
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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