HCID 86592228, compound → HCID 86592227, compound

HRID 1355638Notes

Reaction equation

[CH2:1]([O:3][C:4]([C@H:6]1[CH2:15][C@@H:14]([NH:16]C(OCC2C=CC=CC=2)=O)[C:13]2[C:8](=[CH:9][C:10]([O:29][CH3:30])=[C:11]([O:27][CH3:28])[CH:12]=2)[N:7]1[C:31]([O:33][CH:34]([CH2:36][CH3:37])[CH3:35])=[O:32])=[O:5])[CH3:2]>[Pd].C(O)C.C1CCCCC=1>[CH2:1]([O:3][C:4]([C@H:6]1[CH2:15][C@@H:14]([NH2:16])[C:13]2[C:8](=[CH:9][C:10]([O:29][CH3:30])=[C:11]([O:27][CH3:28])[CH:12]=2)[N:7]1[C:31]([O:33][CH:34]([CH2:36][CH3:37])[CH3:35])=[O:32])=[O:5])[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

cis-4-Benzyloxycarbonylamino-6,7-dimethoxy-3,4-dihydro-2H-quinoline-1,2-dicarboxylic acid 2-butyl ester 1-ethyl ester (Example 2) (800 mg), 10% palladium on carbon (800 mg), and a mixture of ethanol-cyclohexene (2:1, 60 mL) was heated to 70° C. for 2 h. The reaction mixture was cooled to room temperature, filtered through Celite®, and concentrated in vacuo. Purification by silica gel chromatography using to 5% methanol/ethyl acetate afforded the title compound (500 mg). 1H NMR (CDCl3) δ 0.9 (t, 3H), 1.4 (m, 5H), 2.5 (m, 1H), 3.9 (d, 6H), 6.9 (s, 1H), 7.2 (s, 1H).

Workup

temperatureThe reaction mixture was cooled to room temperature
filtrationfiltered through Celite®
concentrationconcentrated in vacuo
customPurification by silica gel chromatography

Sources & evidence

ORD record: ord-8d8a480941eb4a5c87328f97a06edd83
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06586448B1

Reaction notes

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