Diethyl Ether → HCID 59349641, compound

HRID 2090211Notes

Reaction equation

HRID 2090211 reaction equation
[CH2:1]([O:3][C:4]1[N:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]([C:22]1[CH:23]=[CH:24][CH:25]=[C:26]3[C:31]=1[O:30][C:29]([CH3:32])=[CH:28][C:27]3=[O:33])[C:7]([C:15]([O:17]CCC#N)=[O:16])=[C:8]([CH3:14])[NH:9]2)[CH3:2].[OH-].[Na+].C(OCC)C>COCCOC.O>[CH2:1]([O:3][C:4]1[N:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]([C:22]1[CH:23]=[CH:24][CH:25]=[C:26]3[C:31]=1[O:30][C:29]([CH3:32])=[CH:28][C:27]3=[O:33])[C:7]([C:15]([OH:17])=[O:16])=[C:8]([CH3:14])[NH:9]2)[CH3:2]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 68598108HCID 68598108, compound

Product 1

HCID 59349641HCID 59349641, compound

Reagents, catalysts & solvents 1

HCID 18180031Water 1,2-dimethoxyethaneSolvent

Procedure

270 mg (0.61 mmol) of the compound from Example 32A are dissolved in 15 ml of 1,2-dimethoxyethane/water (2:1 v/v), 1.21 ml (1.21 mmol) of 1 N sodium hydroxide solution are added, and the mixture is stirred at room temperature for 1 h. 30 ml of diethyl ether are then added to the reaction mixture. The aqueous phase is separated off and acidified with 1 N hydrochloric acid. The resulting precipitate is filtered off and washed with water and a little diethyl ether. Drying in vacuo at 40° C. results in 167 mg (70% of theory) of the title compound.

Workup

  1. customThe aqueous phase is separated off
  2. filtrationThe resulting precipitate is filtered off
  3. washwashed with water
  4. customDrying in vacuo at 40° C.

Sources & evidence

ORD record
ord-661ca068e1df469eb8aadef23e53c46f
Source dataset
uspto-grants-2013_05
Patent number
US08436180B2

Reaction notes

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