Triethylamine → HCID 67153255, Verbindung

HRID 1879474Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1879474
Cl.[CH3:2][C:3]([CH3:12])([CH3:11])[CH2:4][C@H:5]([NH2:10])[CH2:6][N:7]([CH3:9])[CH3:8].C(N(CC)CC)C.[CH3:20][C@@H:21]1[C@@H:26]([NH:27][C:28]([CH:30]2[CH2:34][CH2:33][S:32](=[O:36])(=[O:35])[N:31]2[CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[C:40]([CH:44]=O)[CH:39]=2)=[O:29])[CH2:25][C@H:24]2[CH2:46][C@@H:22]1[C:23]2([CH3:48])[CH3:47].C([BH3-])#N.[Na+]>CO.C(O)(=O)C>[CH3:20][C@@H:21]1[C@@H:26]([NH:27][C:28]([CH:30]2[CH2:34][CH2:33][S:32](=[O:36])(=[O:35])[N:31]2[CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[C:40]([CH2:44][NH:10][C@H:5]([CH2:6][N:7]([CH3:9])[CH3:8])[CH2:4][C:3]([CH3:12])([CH3:11])[CH3:2])[CH:39]=2)=[O:29])[CH2:25][C@H:24]2[CH2:46][C@@H:22]1[C:23]2([CH3:47])[CH3:48]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 5003444Sodium cyanoborohydrideHCID 86653800HCID 86653800, Verbindung2×HCID 872885452-(3-formyl-benzyl)-1,1-dioxo-1lambda6-isothiazolidine-3-carboxylic acid((1S,2S,3S,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-amide

Produkt 1

HCID 67153255HCID 67153255, VerbindungAusbeute 89,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 887MethanolLösungsmittel2×

Versuchsvorschrift

To a stirred solution of (S)-4,4,N1,N1-tetramethyl-pentane-1,2-diamine hydrochloride salt (Intermediate 2, 0.100 g, 0.43 mmol) in methanol (5 mL) at 0° C. was added triethylamine (0.12 g, 0.16 ml, 1.2 mmol). After 10 min of stirring at the same temperature, a solution of 2-(3-formyl-benzyl)-1,1-dioxo-1λ6-isothiazolidine-3-carboxylic acid((1S,2S,3S,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-amide (0.181 g, 0.43 mmol) in methanol (1 mL) was added and stirring was continued for an additional 15 min at room temperature. The reaction mixture was again brought into 0° C. and sodium cyanoborohydride (0.022 g, 0.35 mmol) and acetic acid (0.2 mL) were added simultaneously into the reaction mixture. After stirring overnight at room temperature, the reaction mixture was concentrated under reduced pressure, the residue was diluted with ethyl acetate (5 mL), washed with water (3 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to provide crude 2-{3-[((S)-1-dimethylaminomethyl-3,3-dimethyl-butylamino)methyl]-benzyl}-1,1-dioxo-1λ6-isothiazolidine-3-carboxylic acid((1S,2S,3S,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-amide (0.216 g, 89%).

Aufarbeitung

  1. stirringstirring
  2. waitwas continued for an additional 15 min at room temperature
  3. customwas again brought into 0° C.
  4. stirringAfter stirring overnight at room temperature
  5. concentrationthe reaction mixture was concentrated under reduced pressure
  6. additionthe residue was diluted with ethyl acetate (5 mL)
  7. washwashed with water (3 mL)
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a36013c528ea45aa96571fe4c13b7c76
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08314250B2

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