Water → HCID 86634376, compound

HRID 1191278Notes

Reaction equation

HRID 1191278 reaction equation
CC(C[Al]CC(C)C)C.[C:10]([O:14][C:15]([NH:17][CH:18]1[CH2:23][CH2:22][CH2:21][N:20]([C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])[CH:19]1[CH2:34][C:35](OCC)=[O:36])=[O:16])([CH3:13])([CH3:12])[CH3:11].O>C1(C)C=CC=CC=1>[C:10]([O:14][C:15]([NH:17][CH:18]1[CH2:23][CH2:22][CH2:21][N:20]([C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])[CH:19]1[CH2:34][CH2:35][OH:36])=[O:16])([CH3:13])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 962WaterHCID 16682954DibahHCID 69009230HCID 69009230, compound

Product 1

HCID 86634376HCID 86634376, compoundYield 67.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
-78 °C

Procedure

1.0 M of a solution (3.15 mL) of Dibal-H in toluene was added dropwise to the compound 13 (440 mg) and toluene (8 mL) with stirring at −78° C. The reaction mixture was stirred at room temperature for 3 hours and then added water at 0° C. Generated salt was removed by filtration with Celite (trade name) and then the filtrate was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and then concentrated. The obtained residue was dissolved in methanol (2 mL) and then sodium borohydride (40 mg) was added into the solution. The reaction solution was stirred at room temperature for 20 minuets, added water and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, concentrated and obtained the title compound (267 mg) having the following physical properties.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 3 hours
  2. customat 0° C
  3. customGenerated salt was removed by filtration with Celite (trade name)
  4. extractionthe filtrate was extracted with ethyl acetate
  5. dry with materialThe extract was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. dissolutionThe obtained residue was dissolved in methanol (2 mL)
  8. additionsodium borohydride (40 mg) was added into the solution
  9. stirringThe reaction solution was stirred at room temperature for 20 minuets
  10. additionadded water
  11. extractionextracted with ethyl acetate
  12. dry with materialThe extract was dried over anhydrous magnesium sulfate
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-3db9ee4dfeab4894b248fcfb984f34b5
Source dataset
uspto-grants-2014_03
Patent number
US08680092B2

Reaction notes

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