Dicyclohexylcarbodiimide → butyl (3S)-2-(3-benzoylthio-2-methylpropionyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate

HRID 127580Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 127580
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C@@H:3]([C:11]([O:13][C:14]([CH3:17])(C)C)=[O:12])[NH:2]1.[C:18]([S:26][CH2:27][CH:28]([CH3:32])[C:29]([OH:31])=O)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.ON1[C:38]2C=CC=C[C:37]=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[C:18]([S:26][CH2:27][CH:28]([CH3:32])[C:29]([N:2]1[C@H:3]([C:11]([O:13][CH2:14][CH2:17][CH2:37][CH3:38])=[O:12])[CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:1]1)=[O:31])(=[O:25])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Komponenten

6

Edukt 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 5694973-(Benzoylthio)-2-methylpropanoic acidHCID 9209323tert-Butyl (3S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate

Produkt 1

HCID 86737593butyl (3S)-2-(3-benzoylthio-2-methylpropionyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylateAusbeute 73,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

3.73 g of tert.-butyl (3S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate, 3.58 g of 3-benzoylthio-2-methylpropionic acid and 2.16 g of 1-hydroxybenzotriazole are dissolved in 60 ml of tetrahydrofuran, and a solution of 3.3 g of dicyclohexylcarbodiimide in 10 ml of tetrahydrofuran is added dropwise thereto at -15° C. After said dropwise addition, the mixture is stirred at a temperature below -10° C. for 3 hours and then at room temperature overnight. Insoluble materials are removed by filtration. The filtrate is distilled under reduced pressure to remove solvent. Water is added to the residue obtained, and the aqueous mixture is extracted with ethyl acetate. The extract is washed with an aqueous 3 % citric acid solution, water, an aqueous sodium bicarbonate solution and water, sucessively. Then, the extract is dried and distilled to remove solvent. The residue thus obtained is purified by silica gel column chromatography. 5.18 g of ter.-butyl (3S)-2-(3-benzoylthio-2-methylpropionyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate are thereby obtained as colorless oil.

Aufarbeitung

  1. customat -15° C
  2. additionaddition
  3. customat room temperature
  4. customovernight
  5. customInsoluble materials are removed by filtration
  6. distillationThe filtrate is distilled under reduced pressure
  7. customto remove solvent
  8. additionWater is added to the residue
  9. customobtained
  10. extractionthe aqueous mixture is extracted with ethyl acetate
  11. washThe extract is washed with an aqueous 3 % citric acid solution, water
  12. customThen, the extract is dried
  13. distillationdistilled
  14. customto remove solvent
  15. customThe residue thus obtained
  16. customis purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d5eece43bbce46a7a5ab4857e0f6da80
Quelldatensatz
uspto-grants-1981_03
Patentnummer
US04256751

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