(S)-9-bromo-5-carboxymethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione → (S)-9-Bromo-5-[p-tert-butoxycarbonylaminomethyl-o-(4-ethoxycarbonylbutyl)phenylcarbamoylmethyl]-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione

HRID 862601Notes

Reaction equation

HRID 862601 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[CH:16]=[C:15]([CH2:17][NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH:14]=[CH:13][C:11]=1[NH2:12])=[O:5])[CH3:2].[Br:26][C:27]1[CH:28]=[C:29]2[CH2:41][CH2:40][C@@H:39]([CH2:42][C:43](O)=[O:44])[N:31]3[C:32](=[O:38])[C:33](=[O:37])[NH:34][C:35]([CH:36]=1)=[C:30]23>C(O)(=O)C.C(OCC)(=O)C>[Br:26][C:27]1[CH:28]=[C:29]2[CH2:41][CH2:40][C@@H:39]([CH2:42][C:43](=[O:44])[NH:12][C:11]3[CH:13]=[CH:14][C:15]([CH2:17][NH:18][C:19]([O:21][C:22]([CH3:24])([CH3:23])[CH3:25])=[O:20])=[CH:16][C:10]=3[CH2:9][CH2:8][CH2:7][CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])[N:31]3[C:32](=[O:38])[C:33](=[O:37])[NH:34][C:35]([CH:36]=1)=[C:30]23

Participants

4

Reactant 2

HCID 10088544(S)-9-bromo-5-carboxymethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dioneHCID 196983622-(4-Ethoxycarbonylbutyl)-4-tert-butoxycarbonylaminomethylaniline

Product 1

HCID 131720496(S)-9-Bromo-5-[p-tert-butoxycarbonylaminomethyl-o-(4-ethoxycarbonylbutyl)phenylcarbamoylmethyl]-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dioneYield 74.5%

Reagents, catalysts & solvents 1

HCID 22609514Ethyl acetate acetateSolvent

Procedure

A procedure similar to that described in Example 18-6) was performed with 2-(4-ethoxycarbonylbutyl)-4-tert-butoxycarbonylaminomethylaniline (256 mg, 0.73 mmol) and (S)-9-bromo-5-carboxymethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione (297 mg, 0.88 mmol) to give 365 mg of the title compound after silica gel column chromatography with 0.3% acetic acid/ethyl acetate (74%).

Sources & evidence

ORD record
ord-0f799ca9c7304ee18bf1581654fe7757
Source dataset
uspto-grants-1998_02
Patent number
US05719152

Reaction notes

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