Ethyl Acetate → HCID 54394959, compound

HRID 1789811Notes

Reaction equation

HRID 1789811 reaction equation
[CH3:1][CH:2]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[H-].[Na+].[C:17]([O:21][C:22](=[O:32])[NH:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30]Br)=[CH:26][N:25]=1)([CH3:20])([CH3:19])[CH3:18].CCOC(C)=O>CN(C=O)C.CCCCCCC.CCOC(C)=O>[CH2:13]([O:12][C:10](=[O:11])[C:2]([CH2:30][C:27]1[CH:26]=[N:25][C:24]([NH:23][C:22]([O:21][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:32])=[CH:29][CH:28]=1)([CH3:1])[C:3]([O:5][C:6]([CH3:8])([CH3:9])[CH3:7])=[O:4])[CH3:14]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 13198666tert-Butyl ethyl methylpropanedioateHCID 23030321tert-Butyl (5-(bromomethyl)pyridin-2-yl)carbamate

Product 1

HCID 54394959HCID 54394959, compoundYield 61.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent3×HCID 21899848Ethylacetate heptaneSolvent

Procedure

A solution of tert-butyl ethyl methylmalonate (457 mg, 2.26 mmol) in DMF (4 mL) was added dropwise to a suspension of NaH (90 mg, 2.26 mmol, 60% in oil) in DMF (4 mL). The reaction mixture was stirred for 20 min. A solution of (5-bromomethyl-pyridin-2-yl)-carbamic acid tert-butyl ester (500 mg, 1.74 mmol) in DMF (2.5 mL) was added and the reaction was stirred for 70 min. EtOAc was added and the mixture was washed with water and brine, dried and concentrated under reduced pressure. Chromathography (Heptane/EtOAc, 3:1→1:3) gave 2-(6-tert-butoxycarbonylamino-pyridin-3-ylmethyl)-2-methyl-malonic acid tert-butyl ester ethyl ester (437 mg, 61% yield).

Workup

  1. stirringthe reaction was stirred for 70 min
  2. washthe mixture was washed with water and brine
  3. customdried
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f8a92e98d3404dbf8bf128e5eee8b1de
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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