Acetic Acid → HCID 22175906, compound

HRID 1797749Notes

Reaction equation

HRID 1797749 reaction equation
[C:1]([O:5][C:6](=[O:34])[NH:7][CH2:8][C:9]1[N:10]([CH2:30][CH:31]([CH3:33])[CH3:32])[C:11](=[O:29])[C:12]2[C:17]([C:18]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[CH:16][C:15]([C:25]([NH:27][NH2:28])=[O:26])=[CH:14][CH:13]=2)([CH3:4])([CH3:3])[CH3:2].[C:35](OC)(OC)(OC)[CH3:36].C1CCN2C(=NCCC2)CC1.C(O)(=O)C>C(O)CCC>[C:1]([O:5][C:6](=[O:34])[NH:7][CH2:8][C:9]1[N:10]([CH2:30][CH:31]([CH3:32])[CH3:33])[C:11](=[O:29])[C:12]2[C:17]([C:18]=1[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[CH:16][C:15]([C:25]1[O:26][C:35]([CH3:36])=[N:28][N:27]=1)=[CH:14][CH:13]=2)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 15050Trimethyl orthoacetateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 22175399HCID 22175399, compound

Product 1

HCID 22175906HCID 22175906, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of tert-butyl[6-(hydrazinocarbonyl)-2-isobutyl-1-oxo-4-phenyl-1,2-dihydro-3-isoquinolinyl]methylcarbamate (0.23 g, 0.50 mmol) and trimethyl orthoacetate (2.0 mL, 11 mmol) in 1-butanol (10 mL) was refluxed for 20 min. To the reaction mixture was added 1,8-diazabicyclo[5.4.0]-7-undecene (0.075 mL, 0.50 mmol), and then the mixture was refluxed for 1 h. The resulting reaction mixture was neutralized with acetic acid (0.040 mL, 0.70 mmol) and concentrated under reduced pressure. The residue was partitioned between water (10 mL) and ethyl acetate (30 mL). The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1 (v/v)) to give tert-butyl[2-isobutyl-6-(5-methyl-1,3,4-oxadiazol-2-yl)-1-oxo-4-phenyl-1,2-dihydro-3-isoquinolinyl]methylcarbamate (0.22 g, 91%) as crystals.

Workup

  1. temperaturewas refluxed for 20 min
  2. temperaturethe mixture was refluxed for 1 h
  3. customThe resulting reaction mixture
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was partitioned between water (10 mL) and ethyl acetate (30 mL)
  6. washThe organic layer was washed with water and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1 (v/v))

Sources & evidence

ORD record
ord-af6069f1005144c68362d297cef52d7f
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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