4-Nitrobenzoic Acid → HCID 70237031, compound

HRID 651547Notes

Reaction equation

HRID 651547 reaction equation
N12CCN(CC1)CC2.[N+:9]([C:12]1[CH:20]=[CH:19][C:15]([C:16]([OH:18])=O)=[CH:14][CH:13]=1)([O-:11])=[O:10].[NH2:21][C@H:22]1[C@@H:34]2[C:35](=[O:38])[O:36][CH2:37][C@H:33]2[C@H:32]([C:39]2[CH:44]=[C:43]([O:45][CH3:46])[C:42]([O:47][Si](C(C)(C)C)(C)C)=[C:41]([O:55][CH3:56])[CH:40]=2)[C:31]2[C:23]1=[CH:24][C:25]1[O:29][CH2:28][O:27][C:26]=1[CH:30]=2>ClCCl>[OH:47][C:42]1[C:43]([O:45][CH3:46])=[CH:44][C:39]([C@@H:32]2[C:31]3[C:23](=[CH:24][C:25]4[O:29][CH2:28][O:27][C:26]=4[CH:30]=3)[C@@H:22]([NH:21][C:16](=[O:18])[C:15]3[CH:14]=[CH:13][C:12]([N+:9]([O-:11])=[O:10])=[CH:20][CH:19]=3)[C@@H:34]3[C:35](=[O:38])[O:36][CH2:37][C@@H:33]23)=[CH:40][C:41]=1[O:55][CH3:56]

Participants

5

Reactant 3

HCID 61084-Nitrobenzoic AcidHCID 9237DabcoHCID 70234588HCID 70234588, compound

Product 1

HCID 70237031HCID 70237031, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.4 mmol of 1,4-diazabicyclo[2.2.2]octane and then 0.78 mmol of para-nitrobenzoic acid are added to a solution of 0.6 mmol of the compound obtained in Step 1 in 10 ml of anhydrous dichloromethane. After 7 hours at ambient temperature, the reaction mixture is evaporated and the residue is chromatographed. The isolated product is then dissolved in 50 ml of methanol and Dowex 50X2-200 resin is added. After stirring for 15 hours at ambient temperature, the reaction mixture is filtered and then concentrated under reduced pressure, enabling the expected product to be isolated.

Workup

  1. customthe reaction mixture is evaporated
  2. customthe residue is chromatographed
  3. dissolutionThe isolated product is then dissolved in 50 ml of methanol
  4. additionDowex 50X2-200 resin is added
  5. filtrationthe reaction mixture is filtered
  6. concentrationconcentrated under reduced pressure
  7. customto be isolated

Sources & evidence

ORD record
ord-db0e9eef470240ada4fb236ab2307b53
Source dataset
uspto-grants-2001_08
Patent number
US06281198B1

Reaction notes

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