Butyl iodide → HCID 23302093, compound

HRID 1291719Notes

Reaction equation

HRID 1291719 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][N:12]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][N:21]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:22][CH2:23][CH2:24][NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[O:7])([CH3:4])([CH3:3])[CH3:2].I[CH2:48][CH2:49][CH2:50][CH3:51]>CN(C=O)C>[CH2:48]([N:25]([C:26]([O:28][C:29]([CH3:30])([CH3:31])[CH3:32])=[O:27])[CH2:24][CH2:23][CH2:22][N:21]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][N:12]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:11][CH2:10][CH2:9][N:8]([CH2:13][CH2:14][CH2:15][CH3:16])[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:49][CH2:50][CH3:51]

Participants

4

Reactant 2

HCID 10962Butyl iodideHCID 14585891HCID 14585891, compound

Product 1

HCID 23302093HCID 23302093, compoundYield 64.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Combine 3.5 gm (0.0053 mol) of the product of Step C of Example 1, 2.7 gm (0.024 mol) of KtBuO, 2.57 ml (0.024 mol) of 1-iodobutane in 10 ml of DMF and allow the mixture to stir for 18 hours. Evaporate the volatiles (0.5 mm at 45° C.), dissolve the residue in 500 ml of EtOAc, water-wash (2× with 100 ml) the organic layer and dry the organic layer over MgSO4. Evaporate off the solvents and subject the residue to flash chromatography (silica gel eluted with 20% EtOAc/hexane to yield 1.32 gm of the title compound. Rf is 0.36 (silica gel plates eluted with 20% EtOAc/hexane).

Workup

  1. customEvaporate the volatiles (0.5 mm at 45° C.)
  2. dissolutiondissolve the residue in 500 ml of EtOAc
  3. washwater-wash (2× with 100 ml) the organic layer
  4. dry with materialdry the organic layer over MgSO4
  5. customEvaporate off the solvents
  6. washeluted with 20% EtOAc/hexane

Sources & evidence

ORD record
ord-94f889bb453b49fcb73c8b03f399fcec
Source dataset
uspto-grants-1998_05
Patent number
US05753714

Reaction notes

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