Methanol → (5S)-9-Bromo-5-[p-tert-butoxycarbonylaminomethyl-o-(1-carboxy-1-hydroxymethyl) phenylcarbamoylmethyl]-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione

HRID 862591Notes

Reaction equation

HRID 862591 reaction equation
[Br: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:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[CH:22][C:21]=3[CH:35]([C:40]([O:42]C)=[O:41])[O:36]C(=O)C)[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23.C1COCC1.CO>[OH-].[Na+]>[Br: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:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[CH:22][C:21]=3[CH:35]([C:40]([OH:42])=[O:41])[OH:36])[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23

Participants

5

Reactant 3

HCID 887MethanolHCID 8028TetrahydrofuranHCID 131720488(5S)-9-Bromo-5-[p-tert-butoxycarbonylaminomethyl-o-(1-methoxycarbonyl-1acetoxymethyl) phenylcarbamoylmethyl]-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione

Product 1

HCID 131720489(5S)-9-Bromo-5-[p-tert-butoxycarbonylaminomethyl-o-(1-carboxy-1-hydroxymethyl) phenylcarbamoylmethyl]-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dioneYield 97.2%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of (5S)-9-bromo-5-[p-tert-butoxycarbonylaminomethyl-o-(1-methoxycarbonyl-1-acetoxymethyl)phenylcarbamoylmethyl]-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione (310 mg, 0.46 mmol) in a mixture of 1N aqueous sodium hydroxide (6 mL), THF (5 mL), and methanol (5 mL) was stirred for 6 h at room temperature. The mixture was concentrated to ca. 6 mL and acidified with 5% aqueous potassium hydrogen sulfate. The precipitates formed were collected and dried to give 276 mg of the title compound (97%).

Workup

  1. concentrationThe mixture was concentrated to ca. 6 mL
  2. customThe precipitates formed
  3. customwere collected
  4. customdried

Sources & evidence

ORD record
ord-7b0e9498b4804b1e960b0bf43e3a1fa0
Source dataset
uspto-grants-1998_02
Patent number
US05719152

Reaction notes

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