Diisopropylethylamine → 1,1-dimethylethyl (2S)-4-{[2-bromo-4-(trifluoromethyl)phenyl]sulfonyl}-2-methyl-1-piperazinecarboxylate

HRID 43379Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 43379
[CH3:1][C@H:2]1[CH2:7][NH:6][CH2:5][CH2:4][N:3]1[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].CCN(C(C)C)C(C)C.[Br:24][C:25]1[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:27][C:26]=1[S:35](Cl)(=[O:37])=[O:36].C([O-])(O)=O.[Na+]>C(Cl)Cl.CCOC(C)=O>[Br:24][C:25]1[CH:30]=[C:29]([C:31]([F:33])([F:32])[F:34])[CH:28]=[CH:27][C:26]=1[S:35]([N:6]1[CH2:5][CH2:4][N:3]([C:8]([O:10][C:11]([CH3:13])([CH3:12])[CH3:14])=[O:9])[C@@H:2]([CH3:1])[CH2:7]1)(=[O:37])=[O:36]

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 27786112-Bromo-4-(trifluoromethyl)benzenesulfonyl chlorideHCID 10081508tert-Butyl (2S)-2-methylpiperazine-1-carboxylate

Produkt 1

HCID 591520681,1-dimethylethyl (2S)-4-{[2-bromo-4-(trifluoromethyl)phenyl]sulfonyl}-2-methyl-1-piperazinecarboxylateAusbeute 80,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 1,1-dimethylethyl (2S)-2-methyl-1-piperazinecarboxylate (1.20 g, 5.99 mmol) and DIPEA (5.45 ml, 31.2 mmol) in dry DCM (60 ml) at 0° C. under Ar was added 2-bromo-4-(trifluoromethyl)benzenesulfonyl chloride (2.04 g, 6.29 mmol) and the resulting clear solution stirred at 0° C. for 2 h. EtOAc (100 ml) and saturated aqueous NaHCO3 (100 ml) were added, the layers separated, then the organic layers washed with 2M aqueous HCl (100 ml) and passed through an hydrophobic frit. The solvent was removed to leave the title compound (2.36 g).

Aufarbeitung

  1. customthe layers separated
  2. washthe organic layers washed with 2M aqueous HCl (100 ml)
  3. customThe solvent was removed

Quellen und Nachweise

ORD-Eintrag
ord-14e44ec0d3f946f6bd250cd0bb94384a
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536183B2

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