Diethyl Ether → HCID 59349653, compound

HRID 2170978Notes

Reaction equation

HRID 2170978 reaction equation
[CH2:1]([O:3][C:4]1[N:13]=[CH:12][C:11]([CH3:14])=[C:10]2[C:5]=1[CH:6]([C:23]1[CH:24]=[CH:25][CH:26]=[C:27]3[C:32]=1[O:31][C:30]([CH3:33])=[CH:29][C:28]3=[O:34])[C:7]([C:16]([O:18]CCC#N)=[O:17])=[C:8]([CH3:15])[NH:9]2)[CH3:2].[OH-].[Na+].C(OCC)C>COCCOC.O>[CH2:1]([O:3][C:4]1[N:13]=[CH:12][C:11]([CH3:14])=[C:10]2[C:5]=1[CH:6]([C:23]1[CH:24]=[CH:25][CH:26]=[C:27]3[C:32]=1[O:31][C:30]([CH3:33])=[CH:29][C:28]3=[O:34])[C:7]([C:16]([OH:18])=[O:17])=[C:8]([CH3:15])[NH:9]2)[CH3:2]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 68602981HCID 68602981, compound

Product 1

HCID 59349653HCID 59349653, compound

Reagents, catalysts & solvents 1

HCID 18180031Water 1,2-dimethoxyethaneSolvent

Procedure

640 mg (1.39 mmol) of the compound from Example 40A are dissolved in 30 ml of 1,2-dimethyoxyethane/water (2:1 v/v), mixed with 2.76 ml (2.76 mmol) of 1 N sodium hydroxide solution and stirred at room temperature for 30 min. The reaction mixture is then mixed with 20 ml of diethyl ether. The aqueous phase is separated off, adjusted to a pH of 4-5 with 1 N hydrochloric acid and extracted three times with ethyl acetate. The organic phases are combined and dried with magnesium sulfate. The volatile components are removed in a rotary evaporator. Drying in vacuo results in 335 mg (56% of theory) of the title compound in a purity of 94% (LC-MS).

Workup

  1. customThe aqueous phase is separated off
  2. extractionextracted three times with ethyl acetate
  3. dry with materialdried with magnesium sulfate
  4. customThe volatile components are removed in a rotary evaporator
  5. customDrying in vacuo

Sources & evidence

ORD record
ord-220beb15ea784427881985d5c13165a8
Source dataset
uspto-grants-2015_06
Patent number
US09051316B2

Reaction notes

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