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

HRID 862577Notes

Reaction equation

HRID 862577 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][C@@H:14]([CH2:17][C:18](=[O:40])[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[CH2:35][C:36]([O:38]C)=[O:37])[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23.C1COCC1.CO.S([O-])(O)(=O)=O.[K+]>S([O-])([O-])(=O)=O.[Na+].[Na+]>[Cl:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][C@@H:14]([CH2:17][C:18](=[O:40])[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[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

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 516920Potassium bisulfateHCID 131720477(S)-9-Chloro-5-[p-tert-butoxycarbonylaminomethyl-o-(methoxycarbonylmethyl)phenylcarbamoylmethyl]-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]-quinoxaline-2,3-dione

Product 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-dioneYield 84.6%

Reagents, catalysts & solvents 1

HCID 24436Sodium SulfateSolvent

Procedure

A solution of (S)-9-chloro-5-[p-tert-butoxycarbonylaminomethyl-o-(methoxycarbonylmethyl)phenylcarbamoylmethyl]-6,7-dihydro-1H, 5H -pyrido[1,2,3-de]quinoxaline-2,3-dione (1.82 g, 3.18 mmol) in a mixture of 1N aqueous sodium sulfate (20 mL), THF (20 mL), and methanol (20 mL) was stirred for 4 h at room temperature. The mixture was acidified to pH 3 by addition of 5% potassium hydrogen sulfate and extracted with a 1:1 mixture of ethyl acetate and THF. The organic layers were washed with brine, dried over magnesium sulfate, and concentrated. The residual solid was washed with dichloromethane, and dried in vacuo to give 1.499 g of the title compound.

Workup

  1. extractionextracted with a 1:1 mixture of ethyl acetate and THF
  2. washThe organic layers were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. washThe residual solid was washed with dichloromethane
  6. customdried in vacuo

Sources & evidence

ORD record
ord-e199e6eaff1a4c999ee7d1a1939c2f1f
Source dataset
uspto-grants-1998_02
Patent number
US05719152

Reaction notes

Loading…