Tetrahydrofuran → HCID 178458159, compound

HRID 1061896Notes

Reaction equation

HRID 1061896 reaction equation
[OH:1][C:2]([C:29]1[CH:43]=[CH:42][C:32]2[C:33]3[CH2:34][N:35]([CH3:41])[C:36](=[O:40])[C:37]=3[CH:38]=[CH:39][C:31]=2[CH:30]=1)([C:5]1[N:6]=[CH:7][N:8](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:9]=1)[CH2:3][CH3:4].C1COCC1>C(O)=O>[OH:1][C:2]([C:29]1[CH:43]=[CH:42][C:32]2[C:33]3[CH2:34][N:35]([CH3:41])[C:36](=[O:40])[C:37]=3[CH:38]=[CH:39][C:31]=2[CH:30]=1)([C:5]1[N:6]=[CH:7][NH:8][CH:9]=1)[CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 120741097-[1-hydroxy-1-(1-trityl-1H-imidazol-4-yl)propyl]-2-methyl-1,2-dihydro-3H-benzo[e]isoindol-3-one

Product 1

HCID 178458159HCID 178458159, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
60 °C

Procedure

7-[1-hydroxy-1-(1-trityl-1H-imidazol-4-yl)propyl]-2-methyl-1,2-dihydro-3H-benzo[e]isoindol-3-one (100 mg) was dissolved in 90% formic acid (1 mL) and THF (1 mL) and the mixture was stirred with heating at 60° C. for 30 min. The reaction mixture was concentrated, and saturated aqueous sodium hydrogen carbonate was added to the residue. The mixture was extracted with a mixed solution of ethyl acetate-THF (1:1), dried and concentrated, and the residue was purified by silica gel chromatography to give the title compound (48 mg) as a colorless powder.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionsaturated aqueous sodium hydrogen carbonate was added to the residue
  3. extractionThe mixture was extracted with a mixed solution of ethyl acetate-THF (1:1)
  4. customdried
  5. concentrationconcentrated
  6. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-6f78d793f9cf45b5b261df4dc0b0103b
Source dataset
uspto-grants-2005_11
Patent number
US06960586B2

Reaction notes

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