Water → Tert-butyl{4-butoxy-2-isobutyl-1-oxo-6-[(E)-2-(1,3-thiazol-4-yl)ethenyl]-1,2-dihydro-3-isoquinolinyl}methylcarbamate

HRID 1797735Notes

Reaction equation

HRID 1797735 reaction equation
[Cl-].C1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)[CH2:9][C:10]2[N:11]=[CH:12][S:13][CH:14]=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].[C:33]([O:37][C:38](=[O:63])[NH:39][CH2:40][C:41]1[N:42]([CH2:59][CH:60]([CH3:62])[CH3:61])[C:43](=[O:58])[C:44]2[C:49]([C:50]=1[O:51][CH2:52][CH2:53][CH2:54][CH3:55])=[CH:48][C:47]([CH:56]=O)=[CH:46][CH:45]=2)([CH3:36])([CH3:35])[CH3:34].O>CN(C)C=O>[C:33]([O:37][C:38](=[O:63])[NH:39][CH2:40][C:41]1[N:42]([CH2:59][CH:60]([CH3:61])[CH3:62])[C:43](=[O:58])[C:44]2[C:49]([C:50]=1[O:51][CH2:52][CH2:53][CH2:54][CH3:55])=[CH:48][C:47](/[CH:56]=[CH:9]/[C:10]1[N:11]=[CH:12][S:13][CH:14]=1)=[CH:46][CH:45]=2)([CH3:36])([CH3:34])[CH3:35]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 22175328Triphenyl(1,3-thiazol-4-ylmethyl)phosphonium chlorideHCID 22176124Tert-butyl (4-butoxy-6-formyl-2-isobutyl-oxo-1,2-dihydro-3-isoquinolinyl)methylcarbamate

Product 1

HCID 22175662Tert-butyl{4-butoxy-2-isobutyl-1-oxo-6-[(E)-2-(1,3-thiazol-4-yl)ethenyl]-1,2-dihydro-3-isoquinolinyl}methylcarbamateYield 81.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of triphenyl(1,3-thiazol-4-ylmethyl)phosphonium chloride (0.44 g, 1.1 mmol), potassium carbonate (15 g, 1.1 mmol) and tert-butyl(4-butoxy-6-formyl-2-isobutyl-1-oxo-1,2-dihydro-3-isoquinolinyl)methylcarbamate (0.47 g, 1.1 mol) in N,N-dimethylformamide (10 ml) was stirred at room temperature for 10 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 resulting crystals were recrystallized from ethyl acetate-diisopropyl ether to give tert-butyl{4-butoxy-2-isobutyl-1-oxo-6-[(E)-2-(1,3-thiazol-4-yl)ethenyl]-1,2-dihydro-3-isoquinolinyl}methylcarbamate (0.46 g, 80.7%) 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 resulting crystals were recrystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-f7e34a5deabb45af8102e008c8013593
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

Loading…