Triethylamine → (S)-6-{3-(tert-butoxycarbonylamino)pyrrolidin-1-ylsulfonyl}isoquinoline

HRID 1845953

Reaktionsgleichung

Reaktionsgleichung von HRID 1845953
Cl[S:2]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]=[N:10][CH:9]=[CH:8]2)(=[O:4])=[O:3].Cl.Cl.N[C@@H]1CCN(S(C2C=C3C(=CC=2)C=NC=C3)(=O)=O)C1.[C:36]([O:40][C:41]([NH:43][C@H:44]1[CH2:48][CH2:47][NH:46][CH2:45]1)=[O:42])([CH3:39])([CH3:38])[CH3:37].C(N(CC)CC)C>ClCCl>[C:36]([O:40][C:41]([NH:43][C@H:44]1[CH2:48][CH2:47][N:46]([S:2]([C:5]2[CH:6]=[C:7]3[C:12](=[CH:13][CH:14]=2)[CH:11]=[N:10][CH:9]=[CH:8]3)(=[O:4])=[O:3])[CH2:45]1)=[O:42])([CH3:39])([CH3:37])[CH3:38]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 1514396(3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 55280287Isoquinoline-6-sulfonyl chlorideHCID 66727170(R)-6-(3-aminopyrrolidin-1-ylsulfonyl)isoquinoline dihydrochloride

Produkt 1

HCID 66727094(S)-6-{3-(tert-butoxycarbonylamino)pyrrolidin-1-ylsulfonyl}isoquinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A dichloromethane solution (100 mL) of 6-chlorosulfonylisoquinoline (Reference Compound 2) was added with stirring at room temperature to a solution containing 423 mg of (S)-(−)-3-(tert-butoxycarbonylamino)pyrrolidine dissolved in 20 mL of dichloromethane further supplemented with 0.5 mL of triethylamine, and reacted for 6 hour. The reaction solution was washed with saturated saline and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated, and the obtained crude product was purified by silica gel column chromatography (acetone:hexane=1:2) to obtain 560 mg of the compound of interest as a colorless oil (65%).

Aufarbeitung

  1. customreacted for 6 hour
  2. washThe reaction solution was washed with saturated saline
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated
  6. customthe obtained crude product
  7. customwas purified by silica gel column chromatography (acetone:hexane=1:2)

Quellen und Nachweise

ORD-Eintrag
ord-de958c0ddf41474598828c5ca6db4c47
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08951997B2

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