Water → HCID 22175915, compound

HRID 1797719Notes

Reaction equation

HRID 1797719 reaction equation
[C:1]([O:5][C:6](=[O:37])[NH:7][CH2:8][C:9]1[N:10]([CH2:33][CH:34]([CH3:36])[CH3:35])[C:11](=[O:32])[C:12]2[C:17]([C:18]=1[C:19]1[S:20][CH:21]=[CH:22][CH:23]=1)=[CH:16][C:15](OS(C(F)(F)F)(=O)=O)=[CH:14][CH:13]=2)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[OH2:45].[O:46]1[CH2:50]CC[CH2:47]1>CO.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([O:5][C:6]([NH:7][CH2:8][C:9]1[N:10]([CH2:33][CH:34]([CH3:35])[CH3:36])[C:11](=[O:32])[C:12]2[C:17]([C:18]=1[C:19]1[S:20][CH:21]=[CH:22][CH:23]=1)=[CH:16][C:15]([C:47]([O:46][CH3:50])=[O:45])=[CH:14][CH:13]=2)=[O:37])([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 22175510HCID 22175510, compound

Product 1

HCID 22175915HCID 22175915, compoundYield 87.2%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of tert-butyl[2-isobutyl-1-oxo-4-(2-thienyl)-6-trifluoromethanesulfonyloxy-1,2-dihydro-3-isoquinolinyl]methylcarbamate (1.40 g, 2.5 mmol), 1,1′-bis(diphenylphosphino)ferrocene (66 mg, 0.12 mmol), triethylamine (0.39 ml, 2.8 mmol) and palladium acetate (27 mg, 0.12 mmol) in tetrahydrofuran (20 ml) and methanol (20 ml) was stirred at 100° C. under a carbon monoxide atmosphere at 5 atom for 3 h. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give methyl 3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-1-oxo-4-(2-thienyl)-1,2-dihydro-6-isoquinolinecarboxylate (1.02 g, 87.2%) as crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-655c7a8ac2234839a5b222aa7a29c433
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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