Neopentyl alcohol → 2,2-Dimethylpropyl 8-(p-chlorophenyl-sulfonamido)-4-[3-(3-pyridyl)-propyl]-octanoate

HRID 465548Notes

Reaction equation

HRID 465548 reaction equation
[CH3:1][C:2]([CH3:6])([CH3:5])[CH2:3][OH:4].C([Li])CCC.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([NH:22][CH2:23][CH2:24][CH2:25][CH2:26][CH:27]([CH2:34][CH2:35][CH2:36][C:37]2[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=2)[CH2:28][CH2:29][C:30](OC)=[O:31])(=[O:21])=[O:20])=[CH:15][CH:14]=1>O1CCCC1.CCCCCC>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([NH:22][CH2:23][CH2:24][CH2:25][CH2:26][CH:27]([CH2:34][CH2:35][CH2:36][C:37]2[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=2)[CH2:28][CH2:29][C:30]([O:4][CH2:3][C:2]([CH3:6])([CH3:5])[CH3:1])=[O:31])(=[O:21])=[O:20])=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 6404Neopentyl alcoholHCID 10479691Methyl 8-(p-chlorophenylsulfonamido)-4-[3-(3-pyridyl)-propyl]-octanoateHCID 178418339Butyllithium

Product 1

HCID 149866682,2-Dimethylpropyl 8-(p-chlorophenyl-sulfonamido)-4-[3-(3-pyridyl)-propyl]-octanoate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a solution of 0.378 g of 2,2-dimethylpropanol in 3 ml tetrahydrofuran is added 0.003 ml of 2.5M n-butyllithium in hexane. To this solution is added 0.332 g methyl 8-(p-chlorophenylsulfonamido)-4-[3-(3-pyridyl)propyl]-octanoate and the mixture is refluxed for 20 h. The reaction is quenched by addition of 3 ml of saturated ammonium chloride solution. It is then extracted with methylene chloride (3×10 ml). The combined organic extracts are dried, filtered and evaporated to dryness to give a clear oil which is purified by preparative thin layer chromatography to obtain 2,2-dimethylpropyl 8-(p-chlorophenylsulfonamido)-4-[3-(3-pyridyl)propyl]-octanoate as a pale yellow oil.

Workup

  1. temperaturethe mixture is refluxed for 20 h
  2. customThe reaction is quenched by addition of 3 ml of saturated ammonium chloride solution
  3. extractionIt is then extracted with methylene chloride (3×10 ml)
  4. customThe combined organic extracts are dried
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customto give a clear oil which
  8. customis purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-d5ede101713e4510820090a1b9a02a97
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

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