Sodium ethoxide → HCID 69237251, compound

HRID 2219580Notes

Reaction equation

HRID 2219580 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:11]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[CH:10][CH:9]=[C:8]([CH2:20][O:21]C(=O)C)[N:7]=1)=[O:5])[CH3:2].CC[O-].[Na+]>C(O)C>[CH2:1]([O:3][C:4]([C:6]1[C:11]([NH:12][C:13]([O:15][C:16]([CH3:18])([CH3:17])[CH3:19])=[O:14])=[CH:10][CH:9]=[C:8]([CH2:20][OH:21])[N:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 69237240HCID 69237240, compound

Product 1

HCID 69237251HCID 69237251, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 0.99 g (2.92 mmol) of 6-Acetoxymethyl-3-tert-butoxycarbonylamino-pyridine-2-carboxylic acid ethyl ester in 15 ml of absolute ethanol was added 0.11 ml (0.3 mmol, 0.1 equiv.) of sodium ethylate 3N /Ethanol. After stirring for 1 h at room temperature, the mixture was extracted with methylene chloride/water. The aqueous phase was extracted three times with methylene chloride. The combined organic phases were dried over magnesium sulfate and concentrated to yield 0.81 g (2.7 mmol, 93%) of the title compound as an off-white solid, MS (ISP): m/e=297.3 (M+H+).

Workup

  1. extractionthe mixture was extracted with methylene chloride/water
  2. extractionThe aqueous phase was extracted three times with methylene chloride
  3. dry with materialThe combined organic phases were dried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6ac25db6ddba45dea2f7da0424543cea
Source dataset
uspto-grants-2008_08
Patent number
US07414060B2

Reaction notes

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