4-Tert-butoxycarbonylaminomethyl-2-(1-methoxycarbonyl-1-acetoxymethyl) aniline → (5S)-9-Chloro-5-[p-tert-butoxycarbonylaminomethyl-o-(1-methoxycarbonyl-1-acetoxymethyl) phenylcarbamoylmethyl]-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione

HRID 862592Notes

Reaction equation

HRID 862592 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:16]=[CH:15][C:13]([NH2:14])=[C:12]([CH:17]([C:22]([O:24][CH3:25])=[O:23])[O:18][C:19](=[O:21])[CH3:20])[CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl: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>>[Cl:26][C:27]1[CH:28]=[C:29]2[CH2:41][CH2:40][C@@H:39]([CH2:42][C:43](=[O:44])[NH:14][C:13]3[CH:15]=[CH:16][C:10]([CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])=[CH:11][C:12]=3[CH:17]([C:22]([O:24][CH3:25])=[O:23])[O:18][C:19](=[O:21])[CH3:20])[N:31]3[C:32](=[O:38])[C:33](=[O:37])[NH:34][C:35]([CH:36]=1)=[C:30]23

Participants

3

Reactant 2

HCID 196983614-Tert-butoxycarbonylaminomethyl-2-(1-methoxycarbonyl-1-acetoxymethyl) anilineHCID 131720478(S)-9-chloro-5-carboxymethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione

Product 1

HCID 131720490(5S)-9-Chloro-5-[p-tert-butoxycarbonylaminomethyl-o-(1-methoxycarbonyl-1-acetoxymethyl) phenylcarbamoylmethyl]-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dioneYield 43.7%

Procedure

A procedure similar to that described in Example 9-7) was performed with 4-tert-butoxycarbonylaminomethyl-2-(1-methoxycarbonyl-1-acetoxymethyl) aniline (500 mg, 1 mmol) and (S)-9-chloro-5-carboxymethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione (413 mg, 1.4 mmol) to give 275 mg of the title compound (43.7%).

Sources & evidence

ORD record
ord-11e9dd9e8807452cb4bd19bed41c0633
Source dataset
uspto-grants-1998_02
Patent number
US05719152

Reaction notes

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