Acetic Acid → 17-Hydroxy-13-methyl-2,14-dioxo-3,13,15-triaza-tricyclo[13.3.0.04,6]octadec-7-ene-4-carboxylic acid ethyl ester

HRID 1443439Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]12[CH2:23][CH:22]1[CH:21]=[CH:20][CH2:19][CH2:18][CH2:17][CH2:16][N:15]([CH3:24])[C:14](=[O:25])[N:13]1[CH:9]([CH2:10][CH:11]([O:26]C(=O)C3C=CC([N+]([O-])=O)=CC=3)[CH2:12]1)[C:8](=[O:38])[NH:7]2)=[O:5])[CH3:2].[OH-].[Li+].C(O)(=O)C>CO.C1COCC1.O>[CH2:1]([O:3][C:4]([C:6]12[CH2:23][CH:22]1[CH:21]=[CH:20][CH2:19][CH2:18][CH2:17][CH2:16][N:15]([CH3:24])[C:14](=[O:25])[N:13]1[CH:9]([CH2:10][CH:11]([OH:26])[CH2:12]1)[C:8](=[O:38])[NH:7]2)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

Compound 50 (200 mg, 0.38 mmol) was dissolved in a mixture of methanol/THF/water, 1:2:1, (20 ml) and cooled on ice-bath. Lithium hydroxide (1.9 ml, 1M) was added slowly. The mixture was stirred for 4 h at 0° C., then neutralized with aqueous acetic acid (20 ml) and extracted with dichloromethane. The organic phase was washed with bicarbonate, water, brine and dried over magnesium sulfate. Purification by chromatography (2% methanol in dichloromethane→4%) gave the title compound as a greyish powder (80%).

Workup

temperaturecooled on ice-bath
extractionextracted with dichloromethane
washThe organic phase was washed with bicarbonate, water, brine
dry with materialdried over magnesium sulfate
customPurification by chromatography (2% methanol in dichloromethane→4%)

Sources & evidence

ORD record: ord-dce5e5675fe14b4b80c71d4fc0ee770d
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07659245B2

Reaction notes

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