L-Alanine → HCID 57473368, compound

HRID 1618172Notes

Reaction equation

HRID 1618172 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 2 N 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-91c8aff76ec5427e9917bf145e8a78fb
Source dataset
uspto-grants-2014_07
Patent number
US08765956B2

Reaction notes

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