Tetrahydrofuran → HCID 57031938, compound

HRID 232133Notes

Reaction equation

HRID 232133 reaction equation
[Cl-].[Li+].C(OP([CH:11]([CH2:15][CH:16]([O:18][CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][O:20]1)[CH3:17])[C:12]([OH:14])=[O:13])(OCC)=O)C.[C:25]1([C:36]2[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]CCC[CH:37]=2)CCCCCCCCNN=1.[CH2:47]([O:54][C:55]([N:57]1[C@@H](CC(C)C)[C@@H](C=O)[O:59][C:58]1([CH3:69])[CH3:68])=[O:56])[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1.O1CC[CH2:72][CH2:71]1>C1C=CC=CC=1>[CH2:47]([O:54][C:55]([N:57]1[C@@H:45]([CH2:46][CH:36]([CH3:25])[CH3:37])[C@H:44]([C:43]([CH2:42][CH3:41])=[C:11]([CH2:15][CH:16]([O:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][O:20]2)[CH3:17])[C:12]([O:14][CH2:71][CH3:72])=[O:13])[O:59][C:58]1([CH3:68])[CH3:69])=[O:56])[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1

Participants

7

Reactant 5

HCID 8028Tetrahydrofuran4×HCID 433294Lithium ChlorideHCID 536302743-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-eneHCID 54296252HCID 54296252, compoundHCID 57130833HCID 57130833, compound

Product 1

HCID 57031938HCID 57031938, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

68 mg of lithium chloride was suspended in 5 ml of dry tetrahydrofuran under an argon stream. Then, a solution prepared by dissolving 0.53 g of 2-diethylphosphono-4-(tetrahydropyran-2-yloxy)pentanoic acid in 1.0 ml of dry tetrahydrofuran, was dropwise added thereto under stirring. The mixture was stirred for 5 minutes, and 0.55 ml of a dry tetrahydrofuran solution of diazabicycloundecene (1/1) was gradually added thereto. The mixture was stirred at room temperature for 10 minutes. Then, a solution prepared by dissolving 385 mg of (4S,5S)-3-benzyloxycarbonyl-4-isobutyl-5-formyl-2,2-dimethyloxazolidine in 2.0 ml of dry tetrahydrofuran, was gradually dropwise added thereto. The mixture was stirred overnight at room temperature. Then, after filtering precipitated inorganic salt off, the reaction solution was neutralized with 1N hydrochloric acid. The reaction, solution was concentrated under reduced pressure, and a syrup thereby obtained was dissolved in 50 ml of benzene, then washed sequentially with 50 ml of water and 50 ml of a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. After filtering the inorganic salt off, the filtrate was concentrated under reduced pressure, and a syrup thereby obtained was purified by silica gel flash column chromatography (Kieselgel (E. Merck No. 9385), developer: hexane/ethyl acetate (10/1 )). The fraction containing the desired product was concentrated and dried under reduced pressure to obtain 454 mg of ethyl 3-[(4S,5S)-3-benzyloxycarbonyl-4-isobutyl-2,2-dimethyloxazolidin-5-yl]-2-[2-(2-tetrahydropyranyloxy)-propyl]-2-pentenoate as a colorless transparent syrup.

Workup

  1. customThen, a solution prepared
  2. additionwas dropwise added
  3. stirringThe mixture was stirred for 5 minutes
  4. stirringThe mixture was stirred at room temperature for 10 minutes
  5. customThen, a solution prepared
  6. additionwas gradually dropwise added
  7. stirringThe mixture was stirred overnight at room temperature
  8. filtrationThen, after filtering
  9. customprecipitated inorganic salt off, the reaction solution
  10. customThe reaction, solution
  11. concentrationwas concentrated under reduced pressure
  12. customa syrup thereby obtained
  13. washwashed sequentially with 50 ml of water and 50 ml of a saturated sodium chloride aqueous solution
  14. dry with materialdried over anhydrous magnesium sulfate
  15. filtrationAfter filtering the inorganic salt off, the filtrate
  16. concentrationwas concentrated under reduced pressure
  17. customa syrup thereby obtained
  18. customwas purified by silica gel flash column chromatography (Kieselgel (E. Merck No. 9385), developer: hexane/ethyl acetate (10/1 ))
  19. additionThe fraction containing the desired product
  20. concentrationwas concentrated
  21. customdried under reduced pressure

Sources & evidence

ORD record
ord-b00380719f46424aa13e569df4cc1cb6
Source dataset
uspto-grants-1989_07
Patent number
US04851387

Reaction notes

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