Dimethylamine, hydrochloride → Benzyl tert-butyl [(1S,2R,4S)-4-(dimethylcarbamoyl)cyclohexane-1,2-diyl]biscarbamate

HRID 459546Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 459546
[C:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([NH:10][C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[C@H:6]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:5]1)(O)=[O:2].Cl.[CH3:30][NH:31][CH3:32].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1>ClCCl.O.C(N(CC)CC)C>[CH2:14]([O:13][C:11]([NH:10][C@H:7]1[CH2:8][CH2:9][C@H:4]([C:1](=[O:2])[N:31]([CH3:32])[CH3:30])[CH2:5][C@H:6]1[NH:21][C:22]([O:24][C:25]([CH3:27])([CH3:26])[CH3:28])=[O:23])=[O:12])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Komponenten

8

Edukt 4

HCID 10473Dimethylamine, hydrochloride2×HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 57416172(1S,3R,4S)-4-{[(Benzyloxy)carbonyl]amino}-3-[(tert-butoxycarbonyl)amino]cyclohexane-1-carboxylic acid

Produkt 1

HCID 57416170Benzyl tert-butyl [(1S,2R,4S)-4-(dimethylcarbamoyl)cyclohexane-1,2-diyl]biscarbamate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8471TriethylamineLösungsmittel2×

Versuchsvorschrift

(1S,2R,4S)-4-Carboxy-N1-benzyloxycarbonyl-N2-(tert-butoxycarbonyl)-1,2-cyclohexanediamine was dissolved in dichloromethane (50 ml), and dimethylamine hydrochloride (240 mg), triethylamine (0.41 ml), 3-(3-dimethylaminopropyl)-1-ethylcarbodiimide hydrochloride (420 mg) and 1-hydroxybenzotriazole monohydrate (340 mg) were added to stir the mixture at room temperature for 1 hour. Dimethylamine hydrochloride (480 mg) and triethylamine (0.82 ml) were additionally added to the reaction mixture to stir the mixture at room temperature for additional 18 hours. The reaction mixture was poured into water to separate an organic layer. After the organic layer was washed with 1N hydrochloric acid and saturated saline and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (methanol:methylene chloride=3:47→2:23) to obtain the title compound (620 mg) as a colorless foamy substance.

Aufarbeitung

  1. stirringto stir the mixture at room temperature for additional 18 hours
  2. customto separate an organic layer
  3. washAfter the organic layer was washed with 1N hydrochloric acid and saturated saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel (methanol:methylene chloride=3:47→2:23)

Quellen und Nachweise

ORD-Eintrag
ord-b3bb12ca48594850a44a7a04e4aa72a4
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07192968B2

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