Water → HCID 59349639, compound

HRID 2090215Notes

Reaction equation

HRID 2090215 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][C:31]([F:34])([F:33])[F:32])[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][C:31]([F:32])([F:33])[F:34])[CH:4]=1)#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 68602934HCID 68602934, compound

Product 1

HCID 59349639HCID 59349639, compound

Reagents, catalysts & solvents 1

HCID 18180031Water 1,2-dimethoxyethaneSolvent

Procedure

1400 mg (2.96 mmol) of the compound from Example 36A are dissolved in 35 ml of 1,2-dimethoxyethane/water (2.5:1 v/v), 5.93 ml (5.93 mmol) of 1 N sodium hydroxide solution are added, and the mixture is stirred at room temperature for 2 h. The reaction mixture is then mixed with 50 ml of diethyl ether and 50 ml of water. The aqueous phase is separated off and adjusted to a pH of 4-5 with 1 N hydrochloric acid. The resulting suspension is then stirred for 1 h. The resulting precipitate is filtered off and washed with water and a little diethyl ether. Drying in vacuo results in 850 mg (68% of theory) of the title compound.

Workup

  1. customThe aqueous phase is separated off
  2. stirringThe resulting suspension is then stirred for 1 h
  3. filtrationThe resulting precipitate is filtered off
  4. washwashed with water
  5. customDrying in vacuo

Sources & evidence

ORD record
ord-a2f4711ca6b64696a1820faf98ab899a
Source dataset
uspto-grants-2013_05
Patent number
US08436180B2

Reaction notes

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