Methanol → HCID 131720475, compound

HRID 862571Notes

Reaction equation

HRID 862571 reaction equation
[Br: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:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[CH:22][C:21]=3[C:35]([O:37]C)=[O:36])[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:39])[NH:19][C:20]3[CH:25]=[CH:24][C:23]([CH2:26][NH:27][C:28]([O:30][C:31]([CH3:33])([CH3:34])[CH3:32])=[O:29])=[CH:22][C:21]=3[C:35]([OH:37])=[O: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 131720476HCID 131720476, compound

Product 1

HCID 131720475HCID 131720475, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of (S)-9-bromo-5-[p-tert-butoxycarbonylaminomethyl-o-(methoxycarbonyl)phenylcarbamoylmethyl]-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione (680 mg, 1.06 mmol) in a mixture of 1N sodium hydroxide (6 mL), THF (6 mL), and methanol (6 mL) was stirred for 3.5 h at room temperature and the solvent was concentrated to ca. 6 mL. To the residue was added 5% potassium hydrogen sulfate and extracted with ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate, and concentrated to give 608 mg of the title compound.

Workup

  1. concentrationthe solvent was concentrated to ca. 6 mL
  2. additionTo the residue was added 5% potassium hydrogen sulfate
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b3602aedc4e8484d8faec3bc28846c83
Source dataset
uspto-grants-1998_02
Patent number
US05719152

Reaction notes

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