Hydrochloric Acid → HCID 66665842, compound

HRID 406201Notes

Reaction equation

HRID 406201 reaction equation
C([O:4][CH:5]1[CH2:28][N:27]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]([O:37]CC)=[O:36])[C:8]2=[N:9][C:10]([C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=3)=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=3)[N:12]=[C:7]2[CH:6]1[O:40]C(=O)C)(=O)C.[Li+].[OH-].Cl>C1COCC1.O>[OH:4][CH:5]1[CH2:28][N:27]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]([OH:37])=[O:36])[C:8]2=[N:9][C:10]([C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=3)=[C:11]([C:13]3[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][CH:18]=3)[N:12]=[C:7]2[CH:6]1[OH:40]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 90354185HCID 90354185, compound

Product 1

HCID 66665842HCID 66665842, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of rac-5-(7-ethoxy-7-oxoheptyl)-2,3-dip-tolyl-5,6,7,8-tetrahydropyrido[2,3-b]pyrazine-7,8-diyl diacetate (step 6) (117 mg, 0.199 mmol) in THF (3 ml) and water (1 ml) was added LiOH (28.6 mg, 1.194 mmol). The mixture was stirred at RT for 18 h followed by heated at 60° C. for 1 h. After cooling to RT, the mixture was acidified to pH 4/5 with 2M HCl and extracted with EtOAc. The combined organic extracts were dried (sodium sulphate), filtered and concentrated in vacuo to afford a mixture of the title products;

Workup

  1. temperatureby heated at 60° C. for 1 h
  2. temperatureAfter cooling to RT
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic extracts were dried (sodium sulphate)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto afford

Sources & evidence

ORD record
ord-9282a204b1c94e6292d99630474489b3
Source dataset
uspto-grants-2014_06
Patent number
US08754085B2

Reaction notes

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