Ethanol → HCID 21401589, compound

HRID 973197Notes

Reaction equation

HRID 973197 reaction equation
[O:1]1[CH2:22][CH:2]1[CH2:3][CH2:4][CH2:5][N:6]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19]CC)=[O:18])[S:7]([CH3:10])(=[O:9])=[O:8].[OH-:23].[Na+].[CH2:25](O)[CH3:26]>O>[OH:23][CH:2]([CH2:22][O:1][CH2:25][CH3:26])[CH2:3][CH2:4][CH2:5][N:6]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])[S:7]([CH3:10])(=[O:8])=[O:9]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 21401575ethyl 7-[N-(4,5-epoxypentyl)methanesulfonamido]heptanoate

Product 1

HCID 21401589HCID 21401589, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of ethyl 7-[N-(4,5-epoxypentyl)- methanesulfonamido]heptanoate (7.0g., 0.02 mole) in ethanol (150 ml.) is added sodium hydroxide (1.84 g., 0.046 mole) dissolved in water (15 ml.). This solution is stirred at room temperature for 18 hours, then concentrated to one-half volume under reduced pressure. Water (150 ml.) is added and this aqueous solution is extracted with ether (2 × 100 ml.). The aqueous layer is then acidified (dilute hydrochloric acid) and extracted with ethyl acetate (2 × 150 ml.). The organic phase is washed with brine, dried over sodium sulfate, then evaporated in vacuo. The yield of subject compound is 4.0 g. (54%) of pale yellow oil.

Workup

  1. concentrationconcentrated to one-half volume under reduced pressure
  2. additionWater (150 ml.) is added
  3. extractionthis aqueous solution is extracted with ether (2 × 100 ml.)
  4. extractionextracted with ethyl acetate (2 × 150 ml.)
  5. washThe organic phase is washed with brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-4426bf2078cb4265afad9b7000ddc2eb
Source dataset
uspto-grants-1977_10
Patent number
US04055596

Reaction notes

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