Water → HCID 67774815, compound

HRID 1963077Notes

Reaction equation

HRID 1963077 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][C:9]([N+]([O-])=O)=[CH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:3]=1[CH3:20].[N+:21]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])#[C-:22].C1CCN2C(=NCCC2)CC1.O>C1COCC1.CC(=O)OCC>[CH2:27]([O:26][C:24]([C:23]1[NH:21][CH:22]=[C:9]([CH2:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=2[CH3:20])[C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:25])[CH3:28]

Participants

7

Reactant 4

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 533707Ethyl isocyanoacetateHCID 67773638HCID 67773638, compound

Product 1

HCID 67774815HCID 67774815, compoundYield 62.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The compound of step 3 (21.45 g, 79.07 mmol) and ethyl isocyanoacetate (10.37 ml, 94.88 mmol) were dissolved in 225 ml of anhydrous THF under a nitrogen atmosphere at 5° C. and DBU (14.16 ml, 94.88 mmol) was added dropwise. The solution was stirred at room temperature for 18 h. Then 200 ml of water and 200 ml of EA were added. The organic phase was washed with 1 N hydrochloric acid (200 ml) and brine (150 ml), dried over magnesium sulfate, filtered and evaporated to dryness under reduced pressure. The residue was purified by chromatography on silica gel (cyclohexane/EA, 90:10, then 85:15) to give 16.68 g of the title compound as a yellow solid melting at 120-122° C.

Workup

  1. washThe organic phase was washed with 1 N hydrochloric acid (200 ml) and brine (150 ml)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated to dryness under reduced pressure
  5. customThe residue was purified by chromatography on silica gel (cyclohexane/EA, 90:10

Sources & evidence

ORD record
ord-7ba9d58585bd4620a8d29bc6c08b9473
Source dataset
uspto-grants-2013_04
Patent number
US08415336B2

Reaction notes

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