Methanol → 5-Cyclopropyl-6-cyclopropylmethoxy-pyridine-2-carboxylic acid [(+)-3-methyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-butyl]-amide

HRID 927685

Reaktionsgleichung

Reaktionsgleichung von HRID 927685
[CH:1]1([C:4]2[CH:5]=[CH:6][C:7]([C:15]([OH:17])=O)=[N:8][C:9]=2[O:10][CH2:11][CH:12]2[CH2:14][CH2:13]2)[CH2:3][CH2:2]1.[CH3:18][C:19]1[O:23][N:22]=[C:21]([CH:24]([CH2:26][CH:27]([CH3:29])[CH3:28])[NH2:25])[N:20]=1.CO>CCCCCCC>[CH3:28][CH:27]([CH3:29])[CH2:26][CH:24]([NH:25][C:15]([C:7]1[CH:6]=[CH:5][C:4]([CH:1]2[CH2:2][CH2:3]2)=[C:9]([O:10][CH2:11][CH:12]2[CH2:13][CH2:14]2)[N:8]=1)=[O:17])[C:21]1[N:20]=[C:19]([CH3:18])[O:23][N:22]=1

Komponenten

5

Edukt 3

HCID 887MethanolHCID 435593295-Methyl-alpha-(2-methylpropyl)-1,2,4-oxadiazole-3-methanamineHCID 710873465-Cyclopropyl-6-cyclopropylmethoxy-pyridine-2-carboxylic acid

Produkt 1

HCID 780101515-Cyclopropyl-6-cyclopropylmethoxy-pyridine-2-carboxylic acid [(+)-3-methyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-butyl]-amide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8900HeptaneLösungsmittel

Versuchsvorschrift

The title compound was synthesized in analogy to Example 1, using 5-cyclopropyl-6-cyclopropylmethyloxy-pyridine-2-carboxylic acid (Example 42a) and 5-methyl-α-(2-methylpropyl)-1,2,4-oxadiazole-3-methanamine (CAN 1155538-06-9) as starting materials. The product was isolated by chiral chromatography on Chiralpak AD using heptane/8% ethanol as eluent. The (−)-enantiomer was isolated. LC-MS (UV peak area/ESI) 100%, 385.2234 (M+H)+, αD20 (MeOH)=−24.8°.

Aufarbeitung

  1. customThe product was isolated by chiral chromatography on Chiralpak AD
  2. customThe (−)-enantiomer was isolated

Quellen und Nachweise

ORD-Eintrag
ord-99c9631457e4467a8aa118bc9b685722
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09290451B2

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