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

HRID 862595Notes

Reaction equation

HRID 862595 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][C@@H:14]([CH2:17][C:18](=[O:44])[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[O:35][CH2:36][C:37]([O:39]C(C)(C)C)=[O:38])[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23>Cl.O1CCOCC1>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][C@@H:14]([CH2:17][C:18](=[O:44])[NH:19][C:20]3[CH:25]=[CH:24][C:23]([CH2:26][NH2:27])=[CH:22][C:21]=3[O:35][CH2:36][C:37]([OH:39])=[O:38])[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23

Participants

4

Reactant 1

HCID 131720491(S)-9-Chloro-5-[p-tert-butoxycarbonylaminomethyl-o-(tert-butoxycarbonylmethoxy) phenylcarbamoylmethyl]-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione

Product 1

HCID 9806306(S)-9-Chloro-5-[p-aminomethyl-o-(carboxymethoxy)phenylcarbamoylmethyl]-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione hydrochlorideYield 171%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

A suspension of (S)-9-chloro-5-[p-tert-butoxycarbonylaminomethyl-o-(tert-butoxycarbonylmethoxy) phenylcarbamoylmethyl]-6,7-dihydro-1H, 5H pyrido[1,2,3-de]quinoxaline-2,3-dione (1.30 g) in 4N hydrogen chloride in 1,4-dioxane (50 mL) was stirred for 20 h at room temperature and 2N hydrochloric acid (35 mL) was added. The mixture was stirred further for 1 h and concentrated in vacuo. The residue was recrystallized from water to give 900 mg of the title compound.

Workup

  1. stirringThe mixture was stirred further for 1 h
  2. concentrationconcentrated in vacuo
  3. customThe residue was recrystallized from water

Sources & evidence

ORD record
ord-29b860c2a58b4561bfbd779ed06b6bca
Source dataset
uspto-grants-1998_02
Patent number
US05719152

Reaction notes

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