Hydrochloric Acid → HCID 12988987, compound

HRID 2086016Notes

Reaction equation

HRID 2086016 reaction equation
CN1CCC[C@H]1C(O)=O.C[O:11][C:12](=[O:35])[C@@H:13]1[CH2:17][CH2:16][CH2:15][N:14]1[C:18]([C:20]1[CH:21]=[CH:22][C:23]2[C:24]3[C:29]([C:30](=[O:34])[NH:31][C:32]=2[CH:33]=1)=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:19].[OH-].[Na+].Cl>C(Cl)Cl.O1CCOCC1>[O:34]=[C:30]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]2[CH:22]=[CH:21][C:20]([C:18]([N:14]3[CH2:15][CH2:16][CH2:17][C@H:13]3[C:12]([OH:35])=[O:11])=[O:19])=[CH:33][C:32]=2[NH:31]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 643474N-Methyl-L-prolineHCID 9968260HCID 9968260, compound

Product 1

HCID 12988987HCID 12988987, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

Prepared from to 3-[6(5H)Phenanthridinone]-carbonyl chloride 7 and (S)-methylproline in methylene chloride according to General Procedure A. The resulting 1-[(5,6-dihydro-6-oxo-3-phenanthridinyl)carbonyl]-proline methyl ester was hydrolyzed with 1N sodium hydroxide in dioxane. After neutralizing the mixture with HCl, the desired compound was collected as a white solid precipitate (60% yield), mp 250-253° C. 1H-NMR (400 MHz, DMSO-d6), 12.60 (bs, 1H), 11.79 (s, 1H), 8.55 9d, 1H, J=8 Hz), 8.47 (d, 1H, J=8 Hz), 8.34 (d, 1H, J=8 Hz), 7.90 (t, 1H, J=8 Hz), 7.70 (t, 1H, J=8Hz), 7.54 (s, 1H), 7.40 (d, 1H, J=8 Hz), 4.44 (m, 1H), 3.56 (m, 2H, 2.37 (m, 1H), 1.90 (m, 3H) Anal. (C19H16N2O2), C H N.

Sources & evidence

ORD record
ord-ecdb1f1d766f413487cea84c9259b6b6
Source dataset
uspto-grants-2004_04
Patent number
US06723733B2

Reaction notes

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