(3,5-Dimethoxyphenyl)methanamine → HCID 57786530, Verbindung

HRID 253562

Reaktionsgleichung

Reaktionsgleichung von HRID 253562
[CH:1]1([CH2:7][C@H:8]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C@H:9]2[CH2:11][O:10]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH:27]=[C:28]([O:30][CH3:31])[CH:29]=1)[CH2:25][NH2:26]>CC#N>[CH:1]1([CH2:7][C@H:8]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C@H:9]([OH:10])[CH2:11][NH:26][CH2:25][C:24]2[CH:27]=[C:28]([O:30][CH3:31])[CH:29]=[C:22]([O:21][CH3:20])[CH:23]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

4

Edukt 2

HCID 420973(3,5-Dimethoxyphenyl)methanamineHCID 9816868erythro-N-Boc-L-cyclohexylalanine epoxide

Produkt 1

HCID 57786530HCID 57786530, VerbindungAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl (S)-2-cyclohexyl-1-((S)-oxiran-2-yl)ethylcarbamate (67.3 mg, 0.25 mmol) in CH3CN (8 mL) was added 3,5-dimethoxybenzylamine (50 mg, 0.3 mmol) and the mixture was heated under reflux overnight. The solvent was removed in vacuo and the residue was purified by the preparative HPLC to give tert-butyl (2S,3R)-1-cyclohexyl-4-(3,5-dimethoxybenzylamino)-3-hydroxybutan-2-ylcarbamate (66.5 mg, 61%). 1H NMR: 0.82 (m, 1H), 0.95 (m, 1H), 1.10-1.48 (m, 6H), 1.42 (s, 9H), 1.65 (m, 4H), 1.80 (m, 1H), 2.67 (m, 2H), 3.46 (m, 1H), 3.64 (m, 1H), 3.72 (d, 2H), 3.79 (s, 6H), 6.35 (m, 1H). MS (E/Z): 437 (M+H+).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux overnight
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by the preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-7f3cb77c95fe4b12997ea5b6b6e7d5a4
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07872028B2

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