Water → HCID 68453456, compound

HRID 499222Notes

Reaction equation

HRID 499222 reaction equation
C(O[C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C@H:10]([CH2:14][N:15]2[CH2:20][CH2:19][N:18]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:17][CH2:16]2)[CH2:9]1)=O)(C)(C)C.O.[OH-].[Na+]>C1COCC1>[CH2:21]([N:18]1[CH2:17][CH2:16][N:15]([CH2:14][C@@H:10]2[CH2:11][CH2:12][CH2:13][N:8]([CH3:6])[CH2:9]2)[CH2:20][CH2:19]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 68457725HCID 68457725, compound

Product 1

HCID 68453456HCID 68453456, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

5 g of the compound obtained in step 3.2 dissolved in 45 ml of THF are added to a solution of 1 g of LiA1H4 in 45 ml of THF cooled to 0° C. The medium is stirred at AT for two hours and then cooled to 0° C. 0.96 ml of water and then 3 ml of 5M NaOH are added, the medium is then filtered, and the solid is rinsed with ether. The filtrate is evaporated, taken up in ether, and washed twice with a saturated NaHCO3 solution and then with a saturated NaCl solution. After drying over MgSO4 and evaporation, 3.5 g of the desired compound are recovered.

Workup

  1. temperaturecooled to 0° C
  2. filtrationthe medium is then filtered
  3. washthe solid is rinsed with ether
  4. customThe filtrate is evaporated
  5. washwashed twice with a saturated NaHCO3 solution
  6. dry with materialAfter drying over MgSO4 and evaporation, 3.5 g of the desired compound
  7. customare recovered

Sources & evidence

ORD record
ord-17cb0c8801d44aa2b3c82759223c2e6e
Source dataset
uspto-grants-2010_08
Patent number
US07767681B2

Reaction notes

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