Diisopropylcarbodiimide → HCID 178453874, Verbindung

HRID 1497028Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1497028
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]([OH:17])=O)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:18][C:19]1[CH:20]=[C:21]([CH:26]=[CH:27][C:28]=1[Cl:29])/[C:22](=[N:24]/O)/[NH2:23].CC(C)N=C=NC(C)C>CN(C1C=CN=CC=1)C.CN(C=O)C.N1C=CC=CC=1.CCOC(C)=O>[Cl:18][C:19]1[CH:20]=[C:21]([C:22]2[N:24]=[C:15]([C@@H:12]3[CH2:11][CH2:10][C@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:14][CH2:13]3)[O:17][N:23]=2)[CH:26]=[CH:27][C:28]=1[Cl:29]

Komponenten

8

Edukt 3

HCID 12734DiisopropylcarbodiimideHCID 112641853,4-Dichloro-N'-hydroxybenzene-1-carboximidamideHCID 178453971HCID 178453971, Verbindung

Produkt 1

HCID 178453874HCID 178453874, VerbindungAusbeute 57,9 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 1049PyridineLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A microwave vial was charged with cis-4-(tert-butoxycarbonylamino)cyclohexanecarboxylic acid (0.24 g, 0.98 mmol), DMAP (0.12 g, 0.98 mmol) and Intermediate 33A (0.20 g, 0.98 mmol). The reactants were dissolved in DMF (1 mL) and DIC (0.15 mL, 0.98 mmol) was added. The reaction mixture was stirred at rt for 14 h. The reaction mixture was diluted in 3 mL of pyridine. The vial was capped and the reaction mixture was heated in the microwave at 145° C. for 20 minutes, allowed to cool to rt, diluted with EtOAc and washed with water and brine. The solution were concentrated under reduced pressure and purified by flash chromatography with EtOAc/hexanes to give Intermediate 33B (233 mg, 0.565 mmol, 57.9% yield) as a white solid. LCMS=434.1 [M+1], RT=2.43 min (Method B); 1H NMR (500 MHz, chloroform-d) δ ppm 8.19 (1H, d, J=1.93 Hz), 7.92 (1H, dd, J=8.53, 1.93 Hz), 7.56 (1H, d, J=8.25 Hz), 4.59 (1H, br. s.), 3.71 (1H, d, J=9.63 Hz), 3.14-3.22 (1H, m), 2.07-2.17 (2H, m), 1.92-2.02 (2H, m), 1.84 (2H, td, J=8.67, 4.13 Hz), 1.62-1.73 (2H, m), 1.44 (9H, s).

Aufarbeitung

  1. customThe vial was capped
  2. temperaturethe reaction mixture was heated in the microwave at 145° C. for 20 minutes
  3. temperatureto cool to rt
  4. washwashed with water and brine
  5. concentrationThe solution were concentrated under reduced pressure
  6. custompurified by flash chromatography with EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-1e1a5803fc7a49bb97c0f57f7e6e582b
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09199946B2

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