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Triethylamine → tert-Butyl (2R)-4-[(6-bromo-1-oxo-1,2-dihydroisoquinolin-4-yl)sulfonyl]-2-(hydroxymethyl)piperazine-1-carboxylate

HRID 906449
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 906449
[OH:1][CH2:2][C@H:3]1[CH2:8][NH:7][CH2:6][CH2:5][N:4]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].C(N(CC)CC)C.[Br:23][C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[C:30](=[O:34])[NH:29][CH:28]=[C:27]2[S:35](Cl)(=[O:37])=[O:36]>C1COCC1>[Br:23][C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[C:30](=[O:34])[NH:29][CH:28]=[C:27]2[S:35]([N:7]1[CH2:6][CH2:5][N:4]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C@@H:3]([CH2:2][OH:1])[CH2:8]1)(=[O:37])=[O:36]
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Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 24820219(R)-2-Hydroxymethyl-piperazine-1-carboxylic acid tert-butyl esterHCID 574399006-Bromo-1-oxo-1,2-dihydroisoquinoline-4-sulfonyl chloride

Produkt 1

HCID 67392085tert-Butyl (2R)-4-[(6-bromo-1-oxo-1,2-dihydroisoquinolin-4-yl)sulfonyl]-2-(hydroxymethyl)piperazine-1-carboxylateAusbeute 76,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel
2×

Versuchsvorschrift

To a solution of tert-butyl (2R)-2-(hydroxymethyl)piperazine-1-carboxylate (0.479 g) and triethylamine (0.618 mL) in THF (6 mL) was added dropwise a solution of 6-bromo-1-oxo-1,2-dihydroisoquinoline-4-sulfonyl chloride (Example 46a, 0.715 g) in THF (10 mL). The reaction was stirred at room temperature for 20 min. The resulting solution was concentrated under reduced pressure before adding water and extracting into ethyl acetate. The combined organics were dried (MgSO4), filtered and evaporated under reduced pressure. Trituration with ethyl acetate gave the subtitle compound (0.855 g).

Aufarbeitung

  1. concentrationThe resulting solution was concentrated under reduced pressure
  2. additionbefore adding water
  3. extractionextracting into ethyl acetate
  4. dry with materialThe combined organics were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-e8b7d749de1247138d8596060c97ce7e
Quelldatensatz
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08012980B2

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