Iodoethane → HCID 15157487, compound

HRID 2371632Notes

Reaction equation

HRID 2371632 reaction equation
[O:1]=[C:2]1[C:7]2[CH:8]=[CH:9][C:10]([O:15][CH2:16][CH2:17][CH2:18][O:19][C:20]3[C:29]4[CH2:28][CH2:27][CH2:26][CH2:25][C:24]=4[CH:23]=[CH:22][CH:21]=3)=[C:11]([CH2:12][CH2:13][CH3:14])[C:6]=2[O:5][C:4]([CH2:35][CH2:36][C:37]([OH:39])=[O:38])([CH2:30][CH2:31][C:32]([OH:34])=[O:33])[CH2:3]1.N12CCCN=C1CCC[CH2:42][CH2:41]2.ICC>CN(C)C=O>[CH2:41]([O:33][C:32](=[O:34])[CH2:31][CH2:30][C:4]1([CH2:35][CH2:36][C:37]([OH:39])=[O:38])[CH2:3][C:2](=[O:1])[C:7]2[CH:8]=[CH:9][C:10]([O:15][CH2:16][CH2:17][CH2:18][O:19][C:20]3[C:29]4[CH2:28][CH2:27][CH2:26][CH2:25][C:24]=4[CH:23]=[CH:22][CH:21]=3)=[C:11]([CH2:12][CH2:13][CH3:14])[C:6]=2[O:5]1)[CH3:42]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 15157460HCID 15157460, compound

Product 1

HCID 15157487HCID 15157487, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the titled product of Example 43 (676 mg, 1.25 mmol) in 5 ml of dimethylformamide (DMF) was added 190 mg (1.25 mmol) of 1,8-diazabicyclo (5.4.0)undec-7-ene followed by 585 mg (3.75 mmol) of iodoethane. After stirring overnight at room temperature, the solvent was removed under reduced pressure. The residue was dissolved in CH2Cl2. The solution was then washed with 3N hydrochloric acid, dried (Na2SO4), filtered, and the solvent removed on a rotary evaporator. The residue was chromatographed on a silica gel column. Elution with 35% ethyl acetate/61.5% hexane/2.5% acetic acid as eluent produced the title product which was crystallized from 3:1 hexane:ethyl acetate to give 183 mg, m.p. 83.5°-84.5° C.

Workup

  1. customthe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in CH2Cl2
  3. washThe solution was then washed with 3N hydrochloric acid
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customthe solvent removed on a rotary evaporator
  7. customThe residue was chromatographed on a silica gel column
  8. washElution with 35% ethyl acetate/61.5% hexane/2.5% acetic acid as eluent

Sources & evidence

ORD record
ord-562def7eee674ae7913c32c032b230c0
Source dataset
uspto-grants-1992_03
Patent number
US05093353

Reaction notes

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