Acetic Acid → HCID 22175296, compound

HRID 1797671Notes

Reaction equation

HRID 1797671 reaction equation
[C:1]([O:5][C:6](=[O:33])[NH:7][CH2:8][C:9]1[N:10]([CH2:29][CH:30]([CH3:32])[CH3:31])[C:11](=[O:28])[C:12]2[C:17]([C:18]=1[O:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:16][C:15]([C:24]([NH2:27])=[N:25][OH:26])=[CH:14][CH:13]=2)([CH3:4])([CH3:3])[CH3:2].[C:34](OC(=O)C)(=O)[CH3:35].C(O)(=O)C.O>O1CCCC1>[C:1]([O:5][C:6](=[O:33])[NH:7][CH2:8][C:9]1[N:10]([CH2:29][CH:30]([CH3:32])[CH3:31])[C:11](=[O:28])[C:12]2[C:17]([C:18]=1[O:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:16][C:15]([C:24]1[N:27]=[C:34]([CH3:35])[O:26][N:25]=1)=[CH:14][CH:13]=2)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 7918Acetic AnhydrideHCID 86592077HCID 86592077, compound

Product 1

HCID 22175296HCID 22175296, compoundYield 45.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyl[6-[amino(hydroxyimino)methyl]-4-butoxy-2-isobutyl-1-oxo-1,2-dihydro-3-isoquinolinyl]methylcarbamate (0.46 g, 1 mmol), acetic anhydride (0.14 ml, 1.5 mmol) and a catalytic amount of acetic acid in tetrahydrofuran (10 ml) was refluxed under heating 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 residue was crystallized from ethyl acetate-diisopropyl ether to give tert-butyl[4-butoxy-2-isobutyl-6-(5-methyl-1,2,4-oxadiazol-3-yl)-1-oxo-1,2-dihydro-3-isoquinolinyl]methylcarbamate (0.22 g, 45.8%) as crystals.

Workup

  1. temperatureunder heating for 10 h
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was crystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-c92a458731f44ffcb7c1710bdbe5cdb8
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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