Dimethylformamide → 4-(cyanomethyl)-N-[(2R)-2-hydroxycyclohexyl]-3-methoxybenzamide

HRID 7796

Reaktionsgleichung

Reaktionsgleichung von HRID 7796
[C:1]([CH2:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=O)=[CH:6][C:5]=1[O:13][CH3:14])#[N:2].C(Cl)(=O)C(Cl)=O.CN(C=O)C.Cl.[NH2:27][C@@H:28]1[CH2:33][CH2:32][CH2:31][CH2:30][C@H:29]1[OH:34]>ClCCl>[C:1]([CH2:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([NH:27][CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][C@H:29]2[OH:34])=[O:10])=[CH:6][C:5]=1[O:13][CH3:14])#[N:2]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 12228412Cyclohexanol, 2-amino-, hydrochloride (1:1), (1R,2R)-HCID 219909984-(Cyanomethyl)-3-methoxybenzoic acid

Produkt 1

HCID 695845884-(cyanomethyl)-N-[(2R)-2-hydroxycyclohexyl]-3-methoxybenzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

The 4-(cyanomethyl)-3-methoxybenzoic acid (0.33 g, 1.7 mmol) was suspended in anhydrous dichloromethane (5 mL) and treated with oxalyl chloride (0.3 mL, 3.5 mmol) followed by few drops of DMF at 22° C. under argon. After 2 h stirring, the resulting solution was concentrated to dryness, dissolved in dichloromethane (5 mL), and added slowly to a solution of trans-2-aminocyclohexanol hydrochloride (0.26 g, 1.7 mmol) and TEA (0.5 mL, 3.5 mmol) in anhydrous dichloromethane (10 mL). After 20 min stirring, filtered off salt, and concentrated to afford 4-(cyanomethyl)-N-[(2R)-2-hydroxycyclohexyl]-3-methoxybenzamide as a yellow solid. MS (ESI) 289 (M+H)+.

Aufarbeitung

  1. concentrationthe resulting solution was concentrated to dryness
  2. dissolutiondissolved in dichloromethane (5 mL)
  3. stirringAfter 20 min stirring
  4. filtrationfiltered off salt
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-8a1abe5c60be4c09bf5242b5d8b1a7a5
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087601B2

Verknüpfte Notizen

Wird geladen…