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Sodium Carbonate → HCID 86676191, Verbindung

HRID 1429674
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1429674
Cl.[NH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7](B(O)O)=[CH:6][CH:5]=1.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH2:22][C@@H:23]3[N:29]([CH:30]=2)[C:28](=[O:31])[C:27]2[CH:32]=[C:33]([O:74][CH3:75])[C:34]([O:36][CH2:37][CH2:38][CH2:39][O:40][C:41]4[C:71]([O:72][CH3:73])=[CH:70][C:44]5[C:45](=[O:69])[N:46]6[CH:61]=[C:60](S(C(F)(F)F)(=O)=O)[CH2:59][C@H:47]6[C:48](=[O:58])[N:49]([CH2:50][O:51][CH2:52][CH2:53][Si:54]([CH3:57])([CH3:56])[CH3:55])[C:43]=5[CH:42]=4)=[CH:35][C:26]=2[N:25]([CH2:76][O:77][CH2:78][CH2:79][Si:80]([CH3:83])([CH3:82])[CH3:81])[C:24]3=[O:84])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.O>[NH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:60]2[CH2:59][C@@H:47]3[N:46]([CH:61]=2)[C:45](=[O:69])[C:44]2[CH:70]=[C:71]([O:72][CH3:73])[C:41]([O:40][CH2:39][CH2:38][CH2:37][O:36][C:34]4[C:33]([O:74][CH3:75])=[CH:32][C:27]5[C:28](=[O:31])[N:29]6[CH:30]=[C:21]([C:18]7[CH:17]=[CH:16][C:15]([O:14][CH3:13])=[CH:20][CH:19]=7)[CH2:22][C@H:23]6[C:24](=[O:84])[N:25]([CH2:76][O:77][CH2:78][CH2:79][Si:80]([CH3:81])([CH3:82])[CH3:83])[C:26]=5[CH:35]=4)=[CH:42][C:43]=2[N:49]([CH2:50][O:51][CH2:52][CH2:53][Si:54]([CH3:57])([CH3:56])[CH3:55])[C:48]3=[O:58])=[CH:6][CH:5]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 27343114-(Aminomethyl)benzeneboronic acid hydrochlorideHCID 86676188HCID 86676188, Verbindung

Produkt 1

HCID 86676191HCID 86676191, VerbindungAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702
Ethanol
Lösungsmittel
HCID 962WaterLösungsmittel
HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
30 °C

Versuchsvorschrift

Solid 4-aminomethylbenzeneboronic acid hydrochloride (0.111 g, 0.59 mmol) was added to a solution of 17 (0.394 g, 0.37 mmol), sodium carbonate (175 mg, 1.654 mmol) and palladium tetrakis triphenylphosphine (28.0 mg, 0.024 mmol) in toluene (10 mL), ethanol (5 mL) and water (5 mL). The reaction mixture was allowed to stir overnight at 30° C. The following day the reaction mixture was heated for a further 3 hours at 70° C. The reaction mixture was then partitioned between ethyl acetate and water. The organic layer was washed with water and brine and dried over magnesium sulphate. Excess solvent was removed by rotary evaporation under reduced pressure and the resulting residue was subjected to flash column chromatography (silica gel; gradient elution EtOAc/hexane 2/9815/85). Removal of excess eluent from selected fractions afforded the desired product (0.230 mg, 0.22 mmol, 61%).

Aufarbeitung

  1. temperatureThe following day the reaction mixture was heated for a further 3 hours at 70° C
  2. customThe reaction mixture was then partitioned between ethyl acetate and water
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulphate
  5. customExcess solvent was removed by rotary evaporation under reduced pressure
  6. washthe resulting residue was subjected to flash column chromatography (silica gel; gradient elution EtOAc/hexane 2/9815/85)
  7. customRemoval of excess eluent

Quellen und Nachweise

ORD-Eintrag
ord-0cb0669eb654438d8a7c3c8d43450557
Quelldatensatz
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08940733B2

Notizen zur Reaktion

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