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Anisole → HCID 58452910, compound

HRID 70657
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Reaction equation

HRID 70657 reaction equation
C1(OC)C=CC=CC=1.[C:9]([C:13]1[CH:18]=[CH:17][C:16](/[C:19](/[C:38]2[NH:43][C:42](=[O:44])[C:41]([CH2:45][CH3:46])=[CH:40][CH:39]=2)=[CH:20]\[C@H:21]2[CH2:25][CH2:24][C:23](=[O:26])[N:22]2CC2C=CC(OC)=CC=2OC)=[CH:15][CH:14]=1)([CH3:12])([CH3:11])[CH3:10]>FC(F)(F)C(O)=O>[C:9]([C:13]1[CH:14]=[CH:15][C:16](/[C:19](/[C:38]2[NH:43][C:42](=[O:44])[C:41]([CH2:45][CH3:46])=[CH:40][CH:39]=2)=[CH:20]\[C@H:21]2[CH2:25][CH2:24][C:23](=[O:26])[NH:22]2)=[CH:17][CH:18]=1)([CH3:12])([CH3:11])[CH3:10]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 7519AnisoleHCID 674000826-{(E)-1-(4-tert-butylphenyl)-2-[(2R)-1-(2,4-dimethoxybenzyl)-5-oxopyrrolidin-2-yl]ethenyl}-3-ethylpyridin-2(1H)-one

Product 1

HCID 58452910HCID 58452910, compoundYield 57.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent2×

Conditions

Temperature
65 °C

Procedure

Anisole (0.25 mL) was added to a solution of 6-{(E)-1-(4-tert-butylphenyl)-2-[(2R)-1-(2,4-dimethoxybenzyl)-5-oxopyrrolidin-2-yl]ethenyl}-3-ethylpyridin-2(1H)-one (49 mg) in trifluoroacetic acid (0.5 mL), and the mixture was stirred at 65° C. for seven hours. Trifluoroacetic acid (0.5 mL) was added and the mixture was stirred for further five hours, after which the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=1:0→9:1). The resulting crystals (25 mg) were recrystallized from ethyl acetate-hexane to give the title compound as a colorless powder (20 mg).

Workup

  1. stirringthe mixture was stirred for further five hours
  2. customafter which the solvent was evaporated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (chloroform:methanol=1:0→9:1)
  4. customThe resulting crystals (25 mg) were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-f7673b04946f4042af1f379061569d09
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08822503B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes