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Dichloromethane → HCID 59540376, compound

HRID 923447
Notes
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Reaction equation

HRID 923447 reaction equation
Br[CH2:2][C:3]1[CH:22]=[CH:21][C:6](/[CH:7]=[CH:8]/[C@@H:9]2[CH2:13][CH2:12][CH2:11][N:10]2[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[CH:5][CH:4]=1.[N+:23]([C:26]1[CH:39]=[CH:38][C:29]([CH2:30][NH:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:28][CH:27]=1)([O-:25])=[O:24].C(=O)([O-])[O-].[K+].[K+].ClCCl>CN(C=O)C>[N+:23]([C:26]1[CH:27]=[CH:28][C:29]([CH2:30][N:31]([CH2:2][C:3]2[CH:22]=[CH:21][C:6](/[CH:7]=[CH:8]/[C@@H:9]3[CH2:13][CH2:12][CH2:11][N:10]3[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[CH:5][CH:4]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:38][CH:39]=1)([O-:25])=[O:24]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 96956N-[(4-nitrophenyl)methyl]anilineHCID 68765291(S,E)-tert-butyl 2-(4-(bromomethyl)styryl)pyrrolidine-1-carboxylate

Product 1

HCID 59540376HCID 59540376, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
50 °C

Procedure

To a solution of the product of Example 149D (1.09 g, 2.97 mmol) and N-(4-nitrobenzyl)aniline (0.677 g, 2.97 mmol) dissolved in DMF (10 mL) was added potassium carbonate (1.23 g, 8.9 mmol) and the mixture heated at 50° C. for 1 hour. After cooling, the solution had dichloromethane added to it and the mixture extracted with water. The organic extract was then dried, filtered, concentrated and purified by chromatography (silica gel, 0-2% methanol in dichloromethane) to afford 0.85 g (56%) of the title compound. MS (ESI) m/z 514 (M+H)+.

Workup

  1. temperatureAfter cooling
  2. additionadded to it
  3. extractionthe mixture extracted with water
  4. extractionThe organic extract
  5. customwas then dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by chromatography (silica gel, 0-2% methanol in dichloromethane)

Sources & evidence

ORD record
ord-510f6c0c406144bea293de0a276194e4
Source dataset
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09278922B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes