Water → HCID 59349645, compound

HRID 2090201Notes

Reaction equation

HRID 2090201 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:18]3[C:13](=[CH:14][CH:15]=[N:16][C:17]=3[O:19][CH2:20][CH3:21])[NH:12][C:11]([CH3:22])=[C:10]2[C:23]([O:25]CCC#N)=[O:24])=[C:5]([O:30][CH3:31])[CH:4]=1)#[N:2].[OH-].[Na+].C(OCC)C.O>COCCOC.O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:18]3[C:13](=[CH:14][CH:15]=[N:16][C:17]=3[O:19][CH2:20][CH3:21])[NH:12][C:11]([CH3:22])=[C:10]2[C:23]([OH:25])=[O:24])=[C:5]([O:30][CH3:31])[CH:4]=1)#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 68600031HCID 68600031, compound

Product 1

HCID 59349645HCID 59349645, compound

Reagents, catalysts & solvents 1

HCID 18180031Water 1,2-dimethoxyethaneSolvent

Procedure

7.20 g (17.21 mmol) of the compound from Example 21A are dissolved in 200 ml of 1,2-dimethoxyethane/water (3:1 v/v), mixed with 34.42 ml (34.42 mmol) of 1 N sodium hydroxide solution and stirred at room temperature overnight. The mixture is then mixed with 100 ml of diethyl ether and 100 ml of water, the organic phase is separated off, and the aqueous phase is adjusted to pH 4-5 with 1N hydrochloric acid. The resulting suspension is stirred for 1 h and the precipitated solid is then removed by filtration. The precipitate is washed with water and a little diethyl ether. Drying in vacuo at 40° C. results in 3.57 g (57% of theory) of the title compound.

Workup

  1. customthe organic phase is separated off
  2. stirringThe resulting suspension is stirred for 1 h
  3. customthe precipitated solid is then removed by filtration
  4. washThe precipitate is washed with water
  5. customDrying in vacuo at 40° C.

Sources & evidence

ORD record
ord-a98086b70605443582c6c8e2c26658f7
Source dataset
uspto-grants-2013_05
Patent number
US08436180B2

Reaction notes

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