Lithium hydroxide, monohydrate → HCID 66987279, compound

HRID 555363Notes

Reaction equation

HRID 555363 reaction equation
C[O:2][C:3](=[O:32])[CH2:4][CH2:5][CH2:6][CH2:7]/[CH:8]=[C:9](\[CH2:20][O:21][C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][CH:23]=1)/[CH2:10][NH:11][CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.O.[OH-].[Li+]>O1CCCC1.O>[O:17]1[CH2:18][CH2:19][N:14]([CH2:13][CH2:12][NH:11][CH2:10]/[C:9](/[CH2:20][O:21][C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:25]=[CH:24][CH:23]=2)=[CH:8]/[CH2:7][CH2:6][CH2:5][CH2:4][C:3]([OH:32])=[O:2])[CH2:15][CH2:16]1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 66986797HCID 66986797, compound

Product 1

HCID 66987279HCID 66987279, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

(Z)-Methyl-8-(2-morpholinoethylamino)-7-((naphthalen-1-yloxy)-methyl)oct-6-enoate (278 mg, 0.63 mmol) obtained in Example (3-1-1) was dissolved in tetrahydrofuran (2.52 ml) in a 25 ml vessel and stirred. To the resulting mixture, a solution of lithium hydroxide monohydrate (LiOH.H2O) (79 mg, 1.89 mmol, 3 eq.) dissolved in water (0.63 ml) was added and stirred at room temperature for 12 hrs. After the completion of reaction, the aqueous layer was washed with ethyl ester and acidified (pH 4) with 6N hydrochloric acid. The resultant was distilled under reduced pressure and extracted with ethyl acetate twice. The organic layer was separated, washed with brine, dried over anhydrous sodium sulfate and filtered. The solvent was removed under reduced pressure. The residue thus obtained was purified with a silica gel column chromatography to obtain 268 mg of the title compound as pale yellow foam (100%).

Workup

  1. additionwas added
  2. stirringstirred at room temperature for 12 hrs
  3. customAfter the completion of reaction
  4. washthe aqueous layer was washed with ethyl ester
  5. distillationThe resultant was distilled under reduced pressure
  6. extractionextracted with ethyl acetate twice
  7. customThe organic layer was separated
  8. washwashed with brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. customThe solvent was removed under reduced pressure
  12. customThe residue thus obtained
  13. customwas purified with a silica gel column chromatography

Sources & evidence

ORD record
ord-08c30c095ea44e2b9d447d2374c368f3
Source dataset
uspto-grants-2011_11
Patent number
US08053435B2

Reaction notes

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