L-Alanine → HCID 57473368, compound

HRID 523696Notes

Reaction equation

HRID 523696 reaction equation
C(O[C:6]([C:8]1[N:9]=[CH:10][C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][CH:14]=[C:13]([O:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)[CH:12]=2)=[O:7])CCC.[NH2:26][C@H:27]([C:29]([OH:31])=[O:30])[CH3:28]>C[O-].[Na+].CO>[CH:20]1([O:19][C:13]2[CH:12]=[C:11]3[C:16]([C:17]([OH:18])=[C:8]([C:6]([NH:26][C@@H:27]([CH3:28])[C:29]([OH:31])=[O:30])=[O:7])[N:9]=[CH:10]3)=[CH:15][CH:14]=2)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

5

Reactant 2

HCID 5950L-AlanineHCID 66712803HCID 66712803, compound

Product 1

HCID 57473368HCID 57473368, compoundYield 62.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 10942334Sodium MethoxideSolvent

Procedure

A mixture of 7-cyclohexyloxyl-4-hydroxy-isoquinoline-3-carboxylic acid butyl ester (80 mg) and L-alanine (207 mg) in 0.5 M sodium methoxide in methanol (3.7 ml) was heated in a microwave reactor (sealed tube) at 120° C. for 40 min. Reaction mixture was concentrated, dissolved in water (30 ml), and acidified by 2N HCl to pH=4. It was extracted with ethyl acetate. Organic layer was washed with water, brine, dried over magnesium sulfate, and filtered. Filtrate was concentrated and purified by silica gel chromatography to give the title compound (52 mg). MS-(+)-ion M+1=359.18.

Workup

  1. temperaturewas heated in a microwave reactor
  2. custom(sealed tube) at 120° C. for 40 min
  3. customReaction mixture
  4. concentrationwas concentrated
  5. dissolutiondissolved in water (30 ml)
  6. extractionIt was extracted with ethyl acetate
  7. washOrganic layer was washed with water, brine
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationFiltrate was concentrated
  11. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-6ff1a5f4032643a4b97ec30e7656d9fb
Source dataset
uspto-grants-2016_05
Patent number
US09339527B2

Reaction notes

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