1-Hydroxybenzotriazole → HCID 89835604, Verbindung

HRID 2277084Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2277084
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][C@H:19]3[C:24](O)=[O:25])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:27]([O:31][C:32](=[O:44])[NH:33][CH2:34][C:35]1[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][C:36]=1[CH2:42][NH2:43])([CH3:30])([CH3:29])[CH3:28].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>CN(C=O)C>[CH:10]1[C:11]2[CH:12]([CH2:14][O:15][C:16]([N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][C@H:19]3[C:24](=[O:25])[NH:43][CH2:42][C:36]3[CH:37]=[C:38]([Cl:41])[CH:39]=[CH:40][C:35]=3[CH2:34][NH:33][C:32]([O:31][C:27]([CH3:30])([CH3:28])[CH3:29])=[O:44])=[O:17])[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

Komponenten

6

Edukt 4

HCID 757711-HydroxybenzotriazoleHCID 9830421-{[(9H-Fluoren-9-yl)methoxy]carbonyl}piperidine-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11149921Tert-butyl 2-(aminomethyl)-4-chlorobenzylcarbamate

Produkt 1

HCID 89835604HCID 89835604, VerbindungAusbeute 76,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of crude (S)-1-[{(9H-Fluoren-9-yl)methoxy}carbonyl]piperidine-2-carboxylic acid (0.75 g, 2.21 mmol), tert-butyl[2-(aminomethyl)-4-chlorobenzyl]carbamate (0.52 g, 1.93 mmol), HOBT (0.26 g, 1.93 mmol), and EDC.HCl (0.48 g, 2.51 mmol) in DMF (5 mL) was stirred under nitrogen at room temperature for 16 h. The reaction mixture was quenched with water (20 mL) and diluted with EtOAc (50 mL). The organic layer was washed sequentially with saturated aqueous NaHCO3 solution (50 mL) and brine solution (50 mL), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by reverse phase combiflash column chromatography (C18; eluent: 10-100% acetonitrile:water) to afford the title compound (0.89 g) as a white solid.

Aufarbeitung

  1. customThe reaction mixture was quenched with water (20 mL)
  2. additiondiluted with EtOAc (50 mL)
  3. washThe organic layer was washed sequentially with saturated aqueous NaHCO3 solution (50 mL) and brine solution (50 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by reverse phase combiflash column chromatography (C18; eluent: 10-100% acetonitrile:water)

Quellen und Nachweise

ORD-Eintrag
ord-700c9a2e625c4353b5a785cf5d3996f7
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09133147B2

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