Water → HCID 136376436, compound

HRID 1797669Notes

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](N1C=CN=C1)(N1C=CN=C1)=[O:35].O>C(OCC)(=O)C>[CH2:20]([O:19][C:18]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:24]3[NH:27][C:34](=[O:35])[O:26][N:25]=3)[CH:16]=2)[C:11](=[O:28])[N:10]([CH2:29][CH:30]([CH3:32])[CH3:31])[C:9]=1[CH2:8][NH:7][C:6](=[O:33])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])[CH2:21][CH2:22][CH3:23]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of tert-butyl[6-[amino(hydroxyimino)methyl]-4-butoxy-2-isobutyl-1-oxo-1,2-dihydro-3-isoquinolinyl]methylcarbamate (0.78 g, 1.7 mmol) in ethyl acetate (10 ml) tetrahydrofuran (10 ml) was added 1,1′-carbonyldiimidazole (0.83 g, 5.1 mmol) and the mixture was stirred at 80° C. for 2 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-1-oxo-6-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)-1,2-dihydro-3-isoquinolinyl]methylcarbamate (0.54 g, 65.9%) as crystals.

Workup

extractionextracted with ethyl acetate
washThe extract was washed with brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was crystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record: ord-86cd35c3a223414d9fef37218f48539f
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07034039B2

Reaction notes

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