Acetic Acid → Diisopropyl Ether

HRID 2243367Notes

Reaction equation

HRID 2243367 reaction equation
[CH3:1][N:2]([CH3:33])[CH2:3][CH2:4][CH2:5][C:6]([O:8][C:9]1[CH:32]=[CH:31][C:12]2[NH:13][C:14]([C:16]3[C:28]4[C:27]5[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=5)[C:21](=[N:29]O)[C:20]=4[CH:19]=[CH:18][CH:17]=3)=[N:15][C:11]=2[CH:10]=1)=[O:7].O.[C:35](O)(=O)C>C(O)C.[Zn]>[CH:9]([O:8][CH:6]([CH3:5])[CH3:35])([CH3:10])[CH3:32].[CH3:33][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][C:6]([O:8][C:9]1[CH:32]=[CH:31][C:12]2[NH:13][C:14]([C:16]3[C:28]4[C:27]5[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=5)[CH:21]([NH2:29])[C:20]=4[CH:19]=[CH:18][CH:17]=3)=[N:15][C:11]=2[CH:10]=1)=[O:7]

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 178483477HCID 178483477, compound

Product 2

HCID 7914Diisopropyl EtherHCID 178483476HCID 178483476, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

The procedure used in Example 216 is followed. In a 20 ml round-bottomed flask under an argon atmosphere, dissolve 468 mg of 4-{5-[(3-dimethylaminopropyl)carbonyloxy]-1H-benzimidazol-2-yl}-9H-fluoren-9-one oxime (Z,E), obtained in the previous stage, in a mixture of 2.5 ml of ethanol, 2.5 ml of water and 2.5 ml acetic acid, at room temperature. Add 278 mg of zinc in three stages. Between each addition, stir for approximately one hour to two hours. Add Celite 545 and filter. The filtrate is concentrated under pressure. After purification by flash chromatography on silica gel (40-63 μm), eluting with a mixture of dichloromethane and ammonia as a 7N solution in methanol (9/1 by volume), and then formation of a paste with diisopropyl ether, in this way we obtain 327 mg of 4-{5-[(3-dimethylaminopropyl)-carbonyloxy]-1H-benzimidazol-2-yl}-9H-fluorene-9(R,S)-amine, in the form of an off-white solid, which is used as it is in the following stage, with the following characteristics:

Workup

  1. additionBetween each addition
  2. filtrationAdd Celite 545 and filter
  3. concentrationThe filtrate is concentrated under pressure
  4. customAfter purification by flash chromatography on silica gel (40-63 μm)
  5. washeluting with a mixture of dichloromethane and ammonia as a 7N solution in methanol (9/1 by volume)

Sources & evidence

ORD record
ord-1e3c264ad551439e9a5d0266cc08fdf1
Source dataset
uspto-grants-2010_03
Patent number
US07674795B2

Reaction notes

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