Hydrochloric Acid → HCID 86599556, compound

HRID 750218Notes

Reaction equation

HRID 750218 reaction equation
COC(=O)C=C[C:6]1[N:7]([CH2:24][C:25]2[CH:33]=[CH:32][C:28]3[O:29][CH2:30][O:31][C:27]=3[CH:26]=2)[C:8](=[O:23])[C:9]2[C:14]([C:15]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH:13][C:12]([Br:22])=[CH:11][CH:10]=2.[CH2:35]1[CH2:39][O:38]C[CH2:36]1.[OH-:40].[Na+].Cl>CO>[O:29]1[C:28]2[CH:32]=[CH:33][C:25]([CH2:24][N:7]3[C:6]([C:35](=[CH2:36])[C:39]([OH:38])=[O:40])=[C:15]([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)[C:14]4[C:9](=[CH:10][CH:11]=[C:12]([Br:22])[CH:13]=4)[C:8]3=[O:23])=[CH:26][C:27]=2[O:31][CH2:30]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 69157072HCID 69157072, compound

Product 1

HCID 86599556HCID 86599556, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 3-[2-(benzo[1,3]dioxol-5-ylmethyl)-6-bromo-1-oxo-4-phenyl-1,2-dihydroisoquinolin-3-yl]acrylic acid methyl ester (100 mg), THF (4.0 ml) and methanol (4.0 ml) was added 1N sodium hydroxide (390 μl), and the mixture was stirred at room temperature for 1 hr. The reaction mixture was adjusted to pH 3 with 1N hydrochloric acid and concentrated under reduced pressure. The residue was partitioned between water and ethyl acetate, 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=3/1-1/1) to give the title compound (46 mg) as colorless crystals.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was partitioned between water and ethyl acetate
  3. dry with materialthe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by medium pressure preparative LC (hexane/ethyl acetate=3/1-1/1)

Sources & evidence

ORD record
ord-e3e176295aa3470890d6c2d2cdc0f5ec
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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