Water → HCID 18646202, compound

HRID 2254320Notes

Reaction equation

HRID 2254320 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][C:18]2([CH3:23])[O:22][CH2:21][CH2:20][O:19]2)=[CH:11][CH:10]=1)=[O:7])[CH3:4].O.[Na+].[Cl-].C1[CH2:31][O:30][CH2:29]C1>>[CH3:23][C:18]1([CH2:17][CH2:16][CH2:15][C:12]2[CH:11]=[CH:10][C:9]([N:8]3[CH2:4][C@H:3]([CH2:29][O:30][CH3:31])[O:5][C:6]3=[O:7])=[CH:14][CH:13]=2)[O:19][CH2:20][CH2:21][O:22]1

Participants

6

Reactant 5

HCID 962WaterHCID 5234Sodium ChlorideHCID 8028Tetrahydrofuran3×HCID 24758Sodium hydrideHCID 54208060HCID 54208060, compound

Product 1

HCID 18646202HCID 18646202, compoundYield 30%

Procedure

To a suspension of 1.96 g (0.041 mol) of NaH (50% in oil) in 100 ml of THF, are added 5 g (0.017 mol) of compound 360274 (Method 3--Step 2), dissolved in 25 ml of THF. After 30 min. of stirring at 30° C.-40° C., are added 4.64 g (0.017 mol) of compound 360065 dissolved in 25 ml of THF and the reaction medium is heated at 50° C.-60° C. for 22 h. The reaction medium is cooled and poured on 500 ml of water. The aqueous phase is saturated with NaCl and extracted with ethyl acetate and then with methylene chloride. The organic phases are dried over Na2SO4 and concentrated. The residue is taken up in ethyl ether. After treatment by animal black, the ethereal solution is concentrated and the product is recrystallized from isopropanol alcool with a 30% yield. The obtained product has the same physical characteristics as those obtained by Method 1.

Workup

  1. temperaturethe reaction medium is heated at 50° C.-60° C. for 22 h
  2. temperatureThe reaction medium is cooled
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phases are dried over Na2SO4
  5. concentrationconcentrated
  6. concentrationAfter treatment by animal black, the ethereal solution is concentrated
  7. customthe product is recrystallized from isopropanol alcool with a 30% yield
  8. customthose obtained by Method 1

Sources & evidence

ORD record
ord-c28e80a03ecb46b3bd3c8710fdab98f5
Source dataset
uspto-grants-1993_08
Patent number
US05235063

Reaction notes

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