Methanol → HCID 67210859, compound

HRID 452131Notes

Reaction equation

HRID 452131 reaction equation
[CH2:1]([C:4]1[N:8]([CH2:9][C:10]2[CH:31]=[CH:30][C:13]3/[C:14](=[CH:23]/[C:24]4[NH:28][C:27](=[O:29])[O:26][N:25]=4)/[C:15]4[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=4[CH2:17][CH2:18][C:12]=3[CH:11]=2)[C:7]2[CH:32]=[CH:33][CH:34]=[CH:35][C:6]=2[N:5]=1)[CH2:2][CH3:3].CO.[C:38]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>C1COCC1>[CH2:1]([C:4]1[N:8]([CH2:9][C:10]2[CH:31]=[CH:30][C:13]3/[C:14](=[CH:23]/[C:24]4[N:28]([CH3:38])[C:27](=[O:29])[O:26][N:25]=4)/[C:15]4[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=4[CH2:17][CH2:18][C:12]=3[CH:11]=2)[C:7]2[CH:32]=[CH:33][CH:34]=[CH:35][C:6]=2[N:5]=1)[CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 887MethanolHCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 136337399HCID 136337399, compound

Product 1

HCID 67210859HCID 67210859, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(E)-2-(2-Propylbenzimidazol-1-yl)methyl-5-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)methylene-10,11-dihydro-5H-dibenzo[a,d]cycloheptene (69 mg, 0.15 mmol) obtained in Example 5 and methanol (30 μL, 0.75 mmol) were dissolved in THF (1 mL), polymer-supported triphenylphosphine (150 mg, 0.45 mmol) and di-tert-butyl azodicarboxylate (104 mg, 0.45 mmol) were added at 0° C., and the mixture was stirred at room temperature for 1 hr. The mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=7/3 to 0/10) to give the title compound (compound 6) (65 mg, 92%).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=7/3 to 0/10)

Sources & evidence

ORD record
ord-318e3aa1d58f43b784742ba2043a0645
Source dataset
uspto-grants-2013_07
Patent number
US08486980B2

Reaction notes

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