Butyl iodide → HCID 44181499, compound

HRID 1944111Notes

Reaction equation

HRID 1944111 reaction equation
[H-].[Na+].[CH:3]([O:6][C:7]1[CH:16]=[C:15]2[C:10]([CH2:11][CH2:12][N:13]3[C:19]([C:20]([N:22]4[CH2:28][CH2:27][C:26](=[O:29])[NH:25][CH2:24][CH2:23]4)=[O:21])=[CH:18][C:17]([C:30]4[S:31][CH:32]=[CH:33][CH:34]=4)=[C:14]32)=[CH:9][C:8]=1[O:35][CH3:36])([CH3:5])[CH3:4].I[CH2:38][CH2:39][CH2:40][CH3:41].[NH4+].[Cl-]>CN(C=O)C>[CH2:38]([N:25]1[C:26](=[O:29])[CH2:27][CH2:28][N:22]([C:20]([C:19]2[N:13]3[CH2:12][CH2:11][C:10]4[C:15]([C:14]3=[C:17]([C:30]3[S:31][CH:32]=[CH:33][CH:34]=3)[CH:18]=2)=[CH:16][C:7]([O:6][CH:3]([CH3:5])[CH3:4])=[C:8]([O:35][CH3:36])[CH:9]=4)=[O:21])[CH2:23][CH2:24]1)[CH2:39][CH2:40][CH3:41]

Participants

6

Reactant 4

HCID 10962Butyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 58147586HCID 58147586, compound

Product 1

HCID 44181499HCID 44181499, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (160 mg, 60% dispersion in oil) was added to a solution of the product of example 13 (767 mg) in DMF (24 ml). After stirring for 5 min at room temperature, 1-iodobutane (1.46 ml) was added and stirring was continued for 18 h at 60° C. The reaction mixture was poured in a sat. aqueous NH4Cl solution and extracted with ethyl acetate. The organic layer was washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel in dichloromethane/methanol [100/0→90/0 (v/v)] as eluent.

Workup

  1. stirringstirring
  2. waitwas continued for 18 h at 60° C
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by chromatography on silica gel in dichloromethane/methanol [100/0→90/0 (v/v)] as eluent

Sources & evidence

ORD record
ord-d91abfebe8504cb1868c189d07e48264
Source dataset
uspto-grants-2013_03
Patent number
US08394789B2

Reaction notes

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