Dimethylformamide → ethyl 7-{N-[4-(2-tetrahydropyranyloxy)nonyl]methanesulfonamido}-2-methylheptanoate

HRID 258605Notes

Reaction equation

HRID 258605 reaction equation
[H-].[Na+].CN(C)C=O.[O:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[O:14][CH:15]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:16][CH2:17][CH2:18][NH:19][S:20]([CH3:23])(=[O:22])=[O:21].Br[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH:35]([CH3:41])[C:36]([O:38][CH2:39][CH3:40])=[O:37]>C1C=CC=CC=1.O>[O:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[O:14][CH:15]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:16][CH2:17][CH2:18][N:19]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH:35]([CH3:41])[C:36]([O:38][CH2:39][CH3:40])=[O:37])[S:20]([CH3:23])(=[O:22])=[O:21]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 20327650N-[4-(2-tetrahydropyranyloxy)nonyl]methanesulfonamideHCID 22770549Ethyl 7-bromo-2-methylheptanoate

Product 1

HCID 20327677ethyl 7-{N-[4-(2-tetrahydropyranyloxy)nonyl]methanesulfonamido}-2-methylheptanoate

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 962WaterSolvent

Procedure

A stirred suspension of sodium hydride (57%) (5.0 g., excess) in a solvent mixture of benzene (75 ml.) and dimethylformamide (75 ml.) is treated, over 30 minutes, with N-[4-(2-tetrahydropyranyloxy)nonyl]methanesulfonamide (Example N, Step 4) (32.1 g., 0.1 mole) dissolved in benzene (20 ml.). Stirring is continued for one hour. Then ethyl 7-bromo-2-methylheptanoate (Example L, Step 4) (25.3 g., 0.1 mole) is added dropwise, and the reaction is heated on the steam bath for 6 hours. The cooled reaction mixture is poured into water (400 ml.) and extracted with ethyl acetate (2× 200 ml.). The organic fractions are combined, washed with brine, then dried over sodium sulfate. The solvents are removed in vacuo to give ethyl 7-{N-[4-(2-tetrahydropyranyloxy)nonyl]methanesulfonamido}-2-methylheptanoate as a pale yellow liquid.

Workup

  1. temperaturethe reaction is heated on the steam bath for 6 hours
  2. customThe cooled reaction mixture
  3. extractionextracted with ethyl acetate (2× 200 ml.)
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. customThe solvents are removed in vacuo

Sources & evidence

ORD record
ord-eea642543b6646eabeb709d9aaa5611b
Source dataset
uspto-grants-1977_07
Patent number
US04033996

Reaction notes

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