Potassium Carbonate → HCID 20028646, compound

HRID 1722425Notes

Reaction equation

HRID 1722425 reaction equation
Cl.[C:2]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([NH:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([NH:24]N)=[CH:20][CH:19]=2)=[O:14])=[CH:8][CH:7]=1)(=[O:4])[CH3:3].C(O[CH:29](OCC)[CH2:30][CH2:31][C:32]#[N:33])C.[OH-].[Na+].C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl.C(O)C.CC(=O)OCC.C(O)(=O)C>[C:2]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([NH:15][CH2:16][CH2:17][C:18]2[CH:23]=[C:22]3[C:21](=[CH:20][CH:19]=2)[NH:24][CH:29]=[C:30]3[CH2:31][C:32]#[N:33])=[O:14])=[CH:8][CH:7]=1)(=[O:4])[CH3:3]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 876164,4-DiethoxybutanenitrileHCID 14180973HCID 14180973, compound

Product 1

HCID 20028646HCID 20028646, compoundYield 5.8%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolventHCID 21584144Dichloromethane ethanolSolvent

Procedure

The compound of Example 29 Section (c) (1.5 g) was suspended in aqueous 25% acetic acid (10 ml) and 3-cyanopropanal diethyl acetal (0.237 g) was added. The mixture was heated at 80° for 2.5 h. The cooled reaction mixture was poured into NaOH solution (2N, 15 ml) and EA (15 ml) cooled in an ice-bath. K2CO3 (2 g) was added portionwise and the layers were separated. The aqueous layer was washed with EA (25 ml) and the combined organic extracts were dried (MgSO4) and evaporated in vacuo to give a yellow oil. The oil was dissolved in CH2Cl2 /ethanol/aqueous NH3 (200:8:1) and flash chromatographed using the same solvent system to give the title compound (33 mg) as a white solid, m.p. 187.5°-189°.

Workup

  1. additionwas added
  2. temperatureThe mixture was heated at 80° for 2.5 h
  3. customThe cooled reaction mixture
  4. temperaturecooled in an ice-bath
  5. customthe layers were separated
  6. washThe aqueous layer was washed with EA (25 ml)
  7. dry with materialthe combined organic extracts were dried (MgSO4)
  8. customevaporated in vacuo
  9. customto give a yellow oil
  10. customflash chromatographed

Sources & evidence

ORD record
ord-de26c7ba32f34cb4a232dc73edd9b95f
Source dataset
uspto-grants-1989_08
Patent number
US04855314

Reaction notes

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