Water → ethyl 7-[N-(4-acetoxynonyl)methanesulfonamido]heptanoate

HRID 258600Notes

Reaction equation

HRID 258600 reaction equation
[H-].[Na+].[CH3:3][S:4]([NH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])(=[O:6])=[O:5].Cl[CH2:20][CH2:21][CH2:22][CH:23]([O:29][C:30](=[O:32])[CH3:31])[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].O>C1C=CC=CC=1.CN(C)C=O>[C:30]([O:29][CH:23]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:22][CH2:21][CH2:20][N:7]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[S:4]([CH3:3])(=[O:6])=[O:5])(=[O:32])[CH3:31]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 12150839Ethyl 7-(methanesulfonamido)heptanoateHCID 131047161-Chloro-4-acetoxynonane

Product 1

HCID 20327690ethyl 7-[N-(4-acetoxynonyl)methanesulfonamido]heptanoate

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.715 g., 0.0298 mole) is suspended in benzene (30 ml.) and dimethylformamide (30 ml.). Ethyl 7-(methanesulfonamido)heptanoate (6.8 g., 0.0271 mole) (Example O, Step 1) is added and the suspension heated on the steam bath for 15 minutes. After cooling to room temperature, 1-chloro-4-acetoxynonane (6.55 g., 0.0298 mole) (Example A, Step 3) is added over 15 minutes and the resulting solution heated on the steam bath for 20 hours. Then the reaction is poured into water (300 ml.) and extracted with ethyl acetate (3× 100 ml.). The organic layer is washed with brine (2× 50 ml.), dried over sodium sulfate then concentrated in vacuo to an oil which is purified by chromatography on silica gel. The silica gel is eluted with 3% methanol in chloroform and evaporation of the appropriate fraction affords ethyl 7-[N-(4-acetoxynonyl)methanesulfonamido]heptanoate. The yield is 6.0 g. (51%).

Workup

  1. temperaturethe suspension heated on the steam bath for 15 minutes
  2. temperaturethe resulting solution heated on the steam bath for 20 hours
  3. extractionextracted with ethyl acetate (3× 100 ml.)
  4. washThe organic layer is washed with brine (2× 50 ml.)
  5. dry with materialdried over sodium sulfate
  6. concentrationthen concentrated in vacuo to an oil which
  7. customis purified by chromatography on silica gel
  8. washThe silica gel is eluted with 3% methanol in chloroform and evaporation of the appropriate fraction

Sources & evidence

ORD record
ord-c7841865984b4f8d9922f3b38090cba8
Source dataset
uspto-grants-1977_07
Patent number
US04033996

Reaction notes

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