8-Azaspiro[4.5]decane-8-sulfonyl chloride → Methyl (S)-2-(8-azaspiro[4.5]decane-8-sulfonylamino)-4,4-difluoropentanoate

HRID 1913344Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1913344
Cl.[NH2:2][C@@H:3]([CH2:8][C:9]([F:12])([F:11])[CH3:10])[C:4]([O:6][CH3:7])=[O:5].[CH2:13]1[C:17]2([CH2:22][CH2:21][N:20]([S:23](Cl)(=[O:25])=[O:24])[CH2:19][CH2:18]2)[CH2:16][CH2:15][CH2:14]1>C(#N)C>[CH2:13]1[C:17]2([CH2:18][CH2:19][N:20]([S:23]([NH:2][C@@H:3]([CH2:8][C:9]([F:11])([F:12])[CH3:10])[C:4]([O:6][CH3:7])=[O:5])(=[O:25])=[O:24])[CH2:21][CH2:22]2)[CH2:16][CH2:15][CH2:14]1

Komponenten

4

Edukt 2

HCID 579461908-Azaspiro[4.5]decane-8-sulfonyl chlorideHCID 86635604methyl (S)-2-amino-4,4-difluoropentanoate hydrochloride

Produkt 1

HCID 57946321Methyl (S)-2-(8-azaspiro[4.5]decane-8-sulfonylamino)-4,4-difluoropentanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

In a reaction vessel, 100 mg of methyl (S)-2-amino-4,4-difluoropentanoate hydrochloride (0.49 mmol) were admixed with 320 mg of N,O-bis(trimethylsilyl)-acetamide (3.2 eq.) in 3 ml of acetonitrile. The reaction mixture was treated at 100° C. in a microwave for 30 min. 128 mg of 8-azaspiro[4.5]decane-8-sulfonyl chloride (1.1 eq.), dissolved in 2.5 ml of acetonitrile, were then added and the resulting reaction mixture was treated at 100° C. in a microwave for a further 2.5 h. The reaction mixture was concentrated under reduced pressure and the resulting residue was purified by preparative HPLC (gradient: acetonitrile/water and addition of 0.05% TFA). Methyl (S)-2-(8-azaspiro[4.5]decane-8-sulfonylamino)-4,4-difluoropentanoate was obtained as a colorless amorphous material.

Aufarbeitung

  1. additionThe reaction mixture was treated at 100° C. in a microwave for 30 min
  2. additionwere then added
  3. customthe resulting reaction mixture
  4. additionwas treated at 100° C. in a microwave for a further 2.5 h
  5. concentrationThe reaction mixture was concentrated under reduced pressure
  6. customthe resulting residue was purified by preparative HPLC (gradient: acetonitrile/water and addition of 0.05% TFA)

Quellen und Nachweise

ORD-Eintrag
ord-9469a8e262264a28a5863cf54fe038e3
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08609681B2

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