Methanol → HCID 86592081, compound

HRID 1797742Notes

Reaction equation

C1(C)C=CC(S([CH2:10][N+:11]#[C-])(=O)=O)=CC=1.CC(C)([O-])C.[K+].[C:20]([O:24][C:25](=[O:51])[NH:26][CH2:27][C:28]1[N:29]([CH2:46][C:47]([CH3:50])([CH3:49])[CH3:48])[C:30](=[O:45])[C:31]2[C:36]([C:37]=1[O:38][CH2:39][CH2:40][CH2:41][CH3:42])=[CH:35][C:34]([CH:43]=O)=[CH:33][CH:32]=2)([CH3:23])([CH3:22])[CH3:21].CO>COCCOC.O>[C:20]([O:24][C:25](=[O:51])[NH:26][CH2:27][C:28]1[N:29]([CH2:46][C:47]([CH3:49])([CH3:50])[CH3:48])[C:30](=[O:45])[C:31]2[C:36]([C:37]=1[O:38][CH2:39][CH2:40][CH2:41][CH3:42])=[CH:35][C:34]([CH2:43][C:10]#[N:11])=[CH:33][CH:32]=2)([CH3:21])([CH3:22])[CH3:23]

Participants

Conditions

Temperature: -70 °C

Procedure

To a solution of p-toluenesulfonylmetyl isocyanide (0.94 g, 4.8 mmol) in 1,2-dimethoxyethane (20 ml) were added potassium t-butoxide (0.90 g, 8 mmol) and tert-butyl(4-butoxy-6-formyl-2-neopentyl-1-oxo-1,2-dihydro-3-isoquinolinyl)methylcarbamate (1.78 g, 4 mmol) at −70° C., and the mixture was stirred at −70° C. for 1 h. To the mixture was added methanol (30 ml), and the mixture was refluxed for 30 min. 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 tert-butyl[4-butoxy-6-(cyanomethyl)-2-neopentyl-1-oxo-1,2-dihydro-3-isoquinolinyl]methylcarbamate (0.66 g, 36.3%) as an amorphous solid.

Workup

temperaturethe mixture was refluxed for 30 min
extractionextracted with ethyl acetate
washThe extract was washed with brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-c07602311b3d4a288a0f643716819d68
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07034039B2

Reaction notes

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