Dichloromethane → HCID 54536141, compound

HRID 1789812Notes

Reaction equation

HRID 1789812 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:31])[C:7]([CH2:16][C:17]1[CH:18]=[N:19][C:20]([NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[CH:21][CH:22]=1)([CH3:15])[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])C.C(Cl)Cl>C1COCC1.CCO>[C:11]([O:10][C:8](=[O:9])[C:7]([CH2:16][C:17]1[CH:18]=[N:19][C:20]([NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[CH:21][CH:22]=1)([CH3:15])[C:6]([OH:31])=[O:5])([CH3:14])([CH3:12])[CH3:13]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 54394959HCID 54394959, compound

Product 1

HCID 54536141HCID 54536141, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Conditions

Temperature
50 °C

Procedure

1M NaOH (2 mL) was added to a solution of 2-(6-tert-butoxycarbonylamino-pyridin-3-ylmethyl)-2-methyl-malonic acid tert-butyl ester ethyl ester (0.42g, 1.03 mmol) in THF/EtOH (4 mL, 1:1) . The reaction mixture was stirred at 50° C. for 16 h. CH2Cl2 was added and the mixture was washed with 0.5 M HCl and brine and dried. Concentration under reduced pressure gave 2-(6-tert-butoxycarbonylamino-pyridin-3-ylmethyl)-2-methyl-malonic acid mono-tert-butyl ester (348 mg, 89%).

Workup

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

Sources & evidence

ORD record
ord-b21262ed18ac45b1b012ac9c43caf368
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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