Serinol → HCID 11245187, compound

HRID 1618201Notes

Reaction equation

HRID 1618201 reaction equation
C(O[C:6]([C:8]1[N:9]=[C:10]([Cl:23])[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][C:14]([O:19][CH:20]([CH3:22])[CH3:21])=[CH:13][CH:12]=2)=[O:7])CCC.[NH2:24][CH:25]([CH2:28][OH:29])[CH2:26][OH:27]>C(O)C>[OH:27][CH2:26][CH:25]([NH:24][C:6]([C:8]1[N:9]=[C:10]([Cl:23])[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][C:14]([O:19][CH:20]([CH3:21])[CH3:22])=[CH:13][CH:12]=2)=[O:7])[CH2:28][OH:29]

Participants

4

Reactant 2

HCID 68294SerinolHCID 18698144HCID 18698144, compound

Product 1

HCID 11245187HCID 11245187, compoundYield 114.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.035 gm of 1-chloro-4-hydroxy-6-isopropoxy-isoquinoline-3-carboxylic acid butyl ester and 0.088 g of 2-amino-propane-1,3-diol were dissolved in 1 ml of ethanol and the mixture was refluxed for 24 h. The reaction mixture was concentrated and the residue was dissolved in 10 ml of ethyl acetate. The ethyl acetate solution was extracted with 5 ml of aqueous 1 M HCl and water, dried (sodium sulfate) and concentrated to give 0.042 g of a white solid: MS-(+)-ion: 355.1.

Workup

  1. temperaturethe mixture was refluxed for 24 h
  2. concentrationThe reaction mixture was concentrated
  3. dissolutionthe residue was dissolved in 10 ml of ethyl acetate
  4. extractionThe ethyl acetate solution was extracted with 5 ml of aqueous 1 M HCl and water
  5. dry with materialdried (sodium sulfate)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-588bb03bf6f54aa799d2a418b9b429f9
Source dataset
uspto-grants-2014_07
Patent number
US08765956B2

Reaction notes

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