Triethylamine → 2-(3-Acetylthio-2-methylpropionyl)-1-oxo-1,2,3,4-tetrahydro-3-isoquinoline carboxylic acid

HRID 485742Notes

Reaction equation

HRID 485742 reaction equation
C(N(CC)CC)C.[O:8]=[C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH:11]([C:19]([OH:21])=[O:20])[NH:10]1.[C:22]([S:25][CH2:26][CH:27]([CH3:31])[C:28](Cl)=[O:29])(=[O:24])[CH3:23].S(Cl)(Cl)=O>C(#N)C.C1C=CC=CC=1>[C:22]([S:25][CH2:26][CH:27]([CH3:31])[C:28]([N:10]1[CH:11]([C:19]([OH:21])=[O:20])[CH2:12][C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9]1=[O:8])=[O:29])(=[O:24])[CH3:23]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 103458Ethanethioic acid, S-(3-chloro-2-methyl-3-oxopropyl) ester2×HCID 48361591-Oxo-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

Product 1

HCID 135046452-(3-Acetylthio-2-methylpropionyl)-1-oxo-1,2,3,4-tetrahydro-3-isoquinoline carboxylic acid

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6342AcetonitrileSolvent2×

Procedure

1.1 g of triethyl amine was added to a suspension of 1-oxo-1,2,3,4-tetrahydro-3-isoquinoline carboxylic acid (1.0 g) in 10 ml of acetonitrile. The suspension was cooled by ice and a solution of 3-acetylthio-2-methyl propionic chloride in 5 ml of acetonitrile was added drop by drop, the 3-acetylthio-2-methyl propionic chloride being prepared by adding 2.0 g of thionyl chloride to a benzene solution of 3-acethylthio-2-methylpropionic acid (0.85 g), stirring overnight at room temperature and distilling off the solvent and the excess amount of thionyl chloride. The mixture was then stirred for two hours at room temperature, the solvent distilled off, 20 ml of ethylacetate and 10 ml of water added, then the solution was shaken and the organic phase separated. After washing the organic phase, it was dried over anhydrous Glauber's salt, the solvent distilled off and then purified by silicagel column chromatography (benzene-acetic acid; 50:1 V/V) to obtain 1.05 g of 2-(3-acetylthio-2 -methylpropionyl)-1-oxo-1,2,3,4-tetrahydro-3-isoquinoline carboxylic acid as an oily material.

Workup

  1. temperatureThe suspension was cooled by ice
  2. distillationdistilling off the solvent
  3. stirringThe mixture was then stirred for two hours at room temperature
  4. distillationthe solvent distilled off
  5. addition20 ml of ethylacetate and 10 ml of water added
  6. stirringthe solution was shaken
  7. customthe organic phase separated
  8. washAfter washing the organic phase, it
  9. dry with materialwas dried over anhydrous Glauber's salt
  10. distillationthe solvent distilled off
  11. custompurified by silicagel column chromatography (benzene-acetic acid; 50:1 V/V)

Sources & evidence

ORD record
ord-17be1e28937c4db4ba41442d68fa5821
Source dataset
uspto-grants-1985_08
Patent number
US04537967

Reaction notes

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