(S)-9-Chloro-5-[p-tert-butoxycarbonylaminomethyl-o-(carboxymethyl)phenylcarbamoylmethyl]-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione → (S)-9-Chloro-5-[p-aminomethyl-o-(carboxymethyl)phenylcarbamoylmethyl]-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione hydrochloride

HRID 862578Notes

Reaction equation

HRID 862578 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][C@@H:14]([CH2:17][C:18](=[O:39])[NH:19][C:20]3[CH:25]=[CH:24][C:23]([CH2:26][NH:27]C(OC(C)(C)C)=O)=[CH:22][C:21]=3[CH2:35][C:36]([OH:38])=[O:37])[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23>Cl.O1CCOCC1.C(OCC)C>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][C@@H:14]([CH2:17][C:18](=[O:39])[NH:19][C:20]3[CH:25]=[CH:24][C:23]([CH2:26][NH2:27])=[CH:22][C:21]=3[CH2:35][C:36]([OH:38])=[O:37])[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23

Participants

5

Reactant 1

HCID 131720479(S)-9-Chloro-5-[p-tert-butoxycarbonylaminomethyl-o-(carboxymethyl)phenylcarbamoylmethyl]-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione

Product 1

HCID 131720480(S)-9-Chloro-5-[p-aminomethyl-o-(carboxymethyl)phenylcarbamoylmethyl]-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione hydrochlorideYield 187.8%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

A suspension of (S)-9-chloro-5-[p-tert-butoxycarbonylaminomethyl-o-(carboxymethyl)phenylcarbamoylmethyl]-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione (1.499 g) in 2N hydrogen chloride in 1,4-dioxane (30 mL) was stirred overnight at room temperature and diluted with diethyl ether. The precipitates were collected and recrystallized from water to give 1.247 g of the title compound (79%).

Workup

  1. customThe precipitates were collected
  2. customrecrystallized from water

Sources & evidence

ORD record
ord-2536ac6227e14548bd9df62c2b607389
Source dataset
uspto-grants-1998_02
Patent number
US05719152

Reaction notes

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