Hydrochloric Acid → HCID 58967382, compound

HRID 1663202Notes

Reaction equation

HRID 1663202 reaction equation
[NH2:1][C:2]1[CH:22]=[CH:21][CH:20]=[CH:19][C:3]=1[C:4]([NH:6][C@@H:7]([CH2:12][CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[C:8]([O:10][CH3:11])=[O:9])=[O:5].Cl.[CH3:24]N1C(=O)CCC1>O1CCOCC1.O>[CH:13]1([CH2:12][C@H:7]([N:6]2[C:4](=[O:5])[C:3]3[C:2](=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:1]=[CH:24]2)[C:8]([O:10][CH3:11])=[O:9])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 13387N-methyl-2-pyrrolidoneHCID 58967458HCID 58967458, compound

Product 1

HCID 58967382HCID 58967382, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of Compound 22 (1 g, 3.29 mmol) in 15 mL of NMP was added triethoxyorthformate (9.87 mmol), followed by 0.5 mL of 4M HCl in dioxane. The mixture was heated to 100° C. overnight, and then diluted with water and extracted with EtOAc. After removing the solvent, the residue was dissolved in MeOH and 7.9 mL of 2 M LiOH was added. The mixture was stirred for 4 hours and acidified with con. HCl to pH=4-5. The mixture was extracted with EtOAc and dried over MgSO4. Removing the solvent gave Compound 23. [M+H] calc'd for C17H20N2O3, 301; found, 301.

Workup

  1. extractionextracted with EtOAc
  2. customAfter removing the solvent
  3. dissolutionthe residue was dissolved in MeOH
  4. addition7.9 mL of 2 M LiOH was added
  5. extractionThe mixture was extracted with EtOAc
  6. dry with materialdried over MgSO4
  7. customRemoving the solvent

Sources & evidence

ORD record
ord-373ff20313c2417c809727300077cc3c
Source dataset
uspto-grants-2011_10
Patent number
US08034822B2

Reaction notes

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