Methanol → HCID 18333081, compound

HRID 2269759Notes

Reaction equation

HRID 2269759 reaction equation
Cl.[C:2]([O:5]CC)(=[O:4])C.[C:8]1([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16]([N:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:21](C=O)[CH:20]([CH2:30][N:31]3[CH2:35][CH2:34][CH2:33][CH2:32]3)[CH2:19]2)=[O:17])=[CH:10][CH:9]=1.[CH3:42][OH:43]>>[C:2]([OH:5])(=[O:4])[C:42]([OH:17])=[O:43].[C:8]1([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][C:16]([N:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[NH:21][CH:20]([CH2:30][N:31]3[CH2:35][CH2:34][CH2:33][CH2:32]3)[CH2:19]2)=[O:17])=[CH:12][CH:13]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 18333156HCID 18333156, compoundHCID 21866389Hydrogen chloride-ethyl acetate

Product 1

HCID 18333081HCID 18333081, compound

Conditions

Temperature
50 °C

Procedure

4N Hydrochloric acid-ethyl acetate (2 ml) was added to a methanol (10 ml) solution of 4-(3-(4-biphenylyl)propanoyl)-1-formyl-2-(pyrrolidin-1-yl)methyl-1,2,3,4-tetrahydroquinoxaline (320 mg). The reaction mixture was stirred at 50° C. for one hour, then concentrated. 10% Aqueous potassium carbonate solution was added to the residue, which was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, then dried and concentrated. The residue was purified by alumina column chromatography (eluent: hexane to hexane/ethyl acetate=7/1), which was converted into its oxalate. The obtained crystals were washed with methanol-IPE to give the entitled compound (250 mg).

Workup

  1. concentrationconcentrated
  2. addition10% Aqueous potassium carbonate solution was added to the residue, which
  3. extractionwas extracted with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by alumina column chromatography (eluent: hexane to hexane/ethyl acetate=7/1), which
  8. washThe obtained crystals were washed with methanol-IPE

Sources & evidence

ORD record
ord-57e7827d114c401685bc864980499474
Source dataset
uspto-grants-2001_12
Patent number
US06329389B1

Reaction notes

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