Potassium sodium tartarate → HCID 22101899, compound

HRID 1458300Notes

Reaction equation

HRID 1458300 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:9]1[CH2:13][CH:12]([NH:14][C:15](=O)[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23]/[CH:24]=[C:25](/[CH2:27][CH2:28][CH:29]=[C:30]([CH3:32])[CH3:31])\[CH3:26])=[CH:18][CH:17]=2)[CH2:11][N:10]1[CH2:34][CH3:35])[CH3:8].C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>>[CH2:34]([N:10]1[CH2:11][CH:12]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23]/[CH:24]=[C:25](/[CH2:27][CH2:28][CH:29]=[C:30]([CH3:32])[CH3:31])\[CH3:26])=[CH:18][CH:17]=2)[CH2:13][N:9]1[CH2:7][CH3:8])[CH3:35]

Participants

4

Reactant 3

HCID 9855836Potassium sodium tartarateHCID 9908920HCID 9908920, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 22101899HCID 22101899, compoundYield 36.1%

Procedure

To a suspension of lithium aluminum hydride (0.27 g) in tetrahydrofuran anhydride (40 ml) was added a solution of N-(1,2-diethyl-4-pyrazolidinyl)-4-geranyloxybenzamide (0.89 g) in tetrahydrofuran anhydride (10 ml) dropwise while being cooled with ice. After being refluxed with heating for 5 hours, the reaction solution, with aqueous solution of sodium potassium tartrate added thereto, was extracted with dichloromethane. The extract was concentrated under a vacuum and thus obtained residue was purified by silica gel column chromatography (chloroform:methanol=40:1), thereby yielding 0.31 g (36%) of the aimed compound.

Workup

  1. temperaturewhile being cooled with ice
  2. temperatureAfter being refluxed
  3. temperaturewith heating for 5 hours
  4. extractionwas extracted with dichloromethane
  5. concentrationThe extract was concentrated under a vacuum and thus obtained residue
  6. customwas purified by silica gel column chromatography (chloroform:methanol=40:1)

Sources & evidence

ORD record
ord-8c1906f560e148eb8f39309a6747ceea
Source dataset
uspto-grants-1998_12
Patent number
US05849930

Reaction notes

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