Imidazole → HCID 59543005, compound

HRID 1876337Notes

Reaction equation

HRID 1876337 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([NH:11][CH:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)[CH:10]=1)[NH:7][C:6]([C:18]1[S:19][CH2:20][C@@H:21]([CH2:23][CH2:24]O)[N:22]=1)=[CH:5]2.N1C=CN=C1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:50]I>O1CCCC1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([NH:11][CH:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)[CH:10]=1)[NH:7][C:6]([C:18]1[S:19][CH2:20][C@@H:21]([CH2:23][CH2:24][I:50])[N:22]=1)=[CH:5]2

Participants

7

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 25196937HCID 25196937, compound

Product 1

HCID 59543005HCID 59543005, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The compound (3.7 g, 10.2 mmol) prepared in Example 32 was dissolved in tetrahydrofuran (100 ml). Imidazole (2.1 g, 30.6 mmol), triphenylphosphine (4.0 g, 15.3 mmol), and iodine (3.9 g, 15.3 mmol) were added thereto, and the mixture was stirred for 8 h at 0° C.˜room temperature. After completion of the reaction, ethyl acetate (100 ml) was added, and the mixture was washed with water (2×100 ml). The organic layer was concentrated, and the residue was separated by column chromatography to give the title compound (2.0 g, 4.07 mmol, Yield 40%).

Workup

  1. additionwas added
  2. washthe mixture was washed with water (2×100 ml)
  3. concentrationThe organic layer was concentrated
  4. customthe residue was separated by column chromatography

Sources & evidence

ORD record
ord-56358d159bec4bcaac345a8c8b772dd7
Source dataset
uspto-grants-2012_11
Patent number
US08309586B2

Reaction notes

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