Water → HCID 69021064, compound

HRID 1865067

Reaction equation

HRID 1865067 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]=[C:16](S(C2C=CC(C)=CC=2)(=O)=O)[C:17]#[N:18])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1CCN2C(=NCCC2)CC1.[N+:40]([CH2:42][C:43]([O:45][CH2:46][CH3:47])=[O:44])#[C-:41].O>C1COCC1.CCOC(C)=O>[CH2:46]([O:45][C:43]([C:42]1[NH:40][CH:41]=[C:16]([C:17]#[N:18])[C:15]=1[C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:14][CH:13]=1)=[O:44])[CH3:47]

Participants

7

Reactant 4

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 533707Ethyl isocyanoacetateHCID 41927733-(4-Benzyloxy-phenyl)-2-(toluene-4-sulfonyl)-acrylonitrile

Product 1

HCID 69021064HCID 69021064, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-(4-benzyloxy-phenyl)-2-(toluene-4-sulfonyl)-acrylonitrile (250.43 g, 0.643 mol, prepared directly above) in anhydrous THF (2,500 mL) is treated with DBU (385.00 mL, 2.574 mol), followed by ethyl isocyanoacetate (150.00 g, 1.286 mol). The resulting reaction mixture is allowed to stir at room temperature for 2 hours. The reaction mixture is poured into water (4,000 mL) and the resulting solution is separated into 2 equal parts. Each part is extracted with EtOAc (3×800 mL each), then the combined organics are washed with 1N HCl (1,000 mL), water (1,000 mL), and brine (1,000 mL), dried over anhydrous MgSO4, filtered, then concentrated in vacuo to afford an off-white solid. The solid is slurried in EtOAc (200 mL), then treated with excess hexanes, causing a solid to precipitate. The solid is recovered by vacuum filtration, washing with hexanes, and drying under vacuum filtration to afford the title compound (204.21 g, 91% yield) as an off-white solid: 1H NMR (500 MHz; CDCl3) δ 9.44 (bs, 1H), 7.48-7.45 (m, 4H), 7.42-7.38 (m, 3H), 7.36-7.32 (m, 1H), 7.03 (d, 2H), 5.11 (s, 2H), 4.25 (q, 2H), 1.22 (t, 3H); MS(ES) m/z 347.1 (M++H).

Workup

  1. customThe resulting reaction mixture
  2. customthe resulting solution is separated into 2 equal parts
  3. extractionEach part is extracted with EtOAc (3×800 mL each)
  4. washthe combined organics are washed with 1N HCl (1,000 mL), water (1,000 mL), and brine (1,000 mL)
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto afford an off-white solid
  9. customto precipitate
  10. filtrationThe solid is recovered by vacuum filtration
  11. washwashing with hexanes
  12. customdrying under vacuum filtration

Sources & evidence

ORD record
ord-fe1f9a3ce63a4c73b85ebe35eb385e9e
Source dataset
uspto-grants-2009_12
Patent number
US07625932B2

Linked notes

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