Hydrochloric Acid → (+/-)-3-Benzoyl-4-((2-amino-2-ethylhexyl)thio)-1H-pyrrole

HRID 398825Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 398825
[C:1]([C:9]1[C:13]([S:14]C(=O)C2C=CC=CC=2)=[CH:12][N:11]([Si](C(C)C)(C(C)C)C(C)C)[CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl.[CH2:36]([C:40]1([CH2:43][CH3:44])[CH2:42][NH:41]1)[CH2:37][CH2:38][CH3:39]>C(OCC)(=O)C.CO>[C:1]([C:9]1[C:13]([S:14][CH2:42][C:40]([NH2:41])([CH2:43][CH3:44])[CH2:36][CH2:37][CH2:38][CH3:39])=[CH:12][NH:11][CH:10]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 189688783-Benzoyl-4-(benzoylthio)-1-(triisopropylsilyl)pyrroleHCID 217099702-Butyl-2-ethylaziridine

Produkt 1

HCID 18968880(+/-)-3-Benzoyl-4-((2-amino-2-ethylhexyl)thio)-1H-pyrroleAusbeute 86,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of the product from step (c) (24.9 g), 250 ml methanol and 106 ml 1N sodium hydroxide was warmed to reflux for 10 minutes then 1N hydrochloric acid (53 ml) was added followed by 2-butyl-2-ethylaziridine (7.7 g, Synthetic Example 1(f)). After one hour the reaction was diluted with ethyl acetate and washed with 1N sodium hydroxide and then water. The organic layer was dried, filtered and concentrated. The residue was chromatographed on silica gel eluting with ethyl acetate-ethanol (3:1) to give a tan viscous oil (15.32 g). 1H NMR is consistent with proposed structure.

Aufarbeitung

  1. temperaturewas warmed
  2. temperatureto reflux for 10 minutes
  3. washwashed with 1N sodium hydroxide
  4. customThe organic layer was dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel eluting with ethyl acetate-ethanol (3:1)

Quellen und Nachweise

ORD-Eintrag
ord-2066aeb38abe4dcd929312d9f9aefe20
Quelldatensatz
uspto-grants-1998_10
Patentnummer
US05817652

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