Methanol → HCID 69155736, compound

HRID 750250Notes

Reaction equation

HRID 750250 reaction equation
Cl.[C:2]([C:5]1[CH:10]=[C:9]([CH2:11][O:12][C:13]([C:15]2[N:16]([CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:17](=[O:32])[C:18]3[C:23]([C:24]=2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:22][C:21]([Br:31])=[CH:20][CH:19]=3)=[O:14])[CH:8]=[CH:7][N:6]=1)([OH:4])=[O:3].S(=O)(=O)(O)O.[CH3:45]O>>[CH3:45][O:3][C:2]([C:5]1[CH:10]=[C:9]([CH2:11][O:12][C:13]([C:15]2[N:16]([CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:17](=[O:32])[C:18]3[C:23]([C:24]=2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:22][C:21]([Br:31])=[CH:20][CH:19]=3)=[O:14])[CH:8]=[CH:7][N:6]=1)=[O:4]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 69157443HCID 69157443, compound

Product 1

HCID 69155736HCID 69155736, compound

Procedure

To a solution (3.0 ml) of 2-benzyl-6-bromo-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid 2-carboxypyridin-4-ylmethyl ester hydrochloride (120 mg) in methanol was added conc. sulfuric acid (0.3 ml) at 0° C. with stirring, and the mixture was stirred at 50° C. for 48 hrs. After cooling the mixture, the solvent was removed under reduced pressure. The residue was partitioned between ethyl acetate and saturated aqueous sodium hydrogen carbonate, and the organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by medium pressure preparative LC (hexane/ethyl acetate=4/1-1/1) to give the title compound (73 mg) as colorless crystals.

Workup

  1. stirringthe mixture was stirred at 50° C. for 48 hrs
  2. temperatureAfter cooling the mixture
  3. customthe solvent was removed under reduced pressure
  4. customThe residue was partitioned between ethyl acetate and saturated aqueous sodium hydrogen carbonate
  5. dry with materialthe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by medium pressure preparative LC (hexane/ethyl acetate=4/1-1/1)

Sources & evidence

ORD record
ord-1eb558143f5547edb0daa68ed75ffd11
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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