Propargylamine → N-{(1S,2R)-2-[4-(4-Aminomethyl-[1,2,3]triazol-1-yl)-phenyl]-1-fluoromethyl-2-hydroxy-ethyl}-2,2-dichloroacetamide

HRID 1520511

Reaktionsgleichung

Reaktionsgleichung von HRID 1520511
[N:1]([C:4]1[CH:9]=[CH:8][C:7]([C@@H:10]([OH:20])[C@H:11]([NH:14][C:15](=[O:19])[CH:16]([Cl:18])[Cl:17])[CH2:12][F:13])=[CH:6][CH:5]=1)=[N+:2]=[N-:3].[CH2:21]([NH2:24])[C:22]#[CH:23]>C(O)(C)(C)C.O>[NH2:24][CH2:21][C:22]1[N:3]=[N:2][N:1]([C:4]2[CH:9]=[CH:8][C:7]([C@@H:10]([OH:20])[C@H:11]([NH:14][C:15](=[O:19])[CH:16]([Cl:17])[Cl:18])[CH2:12][F:13])=[CH:6][CH:5]=2)[CH:23]=1

Komponenten

4

Edukt 2

HCID 239041PropargylamineHCID 86695459N-[(1S,2R)-2-(4-Azido-phenyl)-1-fluoromethyl-2-hydroxy-ethyl]-2,2-dichloro-acetamide

Produkt 1

HCID 86695460N-{(1S,2R)-2-[4-(4-Aminomethyl-[1,2,3]triazol-1-yl)-phenyl]-1-fluoromethyl-2-hydroxy-ethyl}-2,2-dichloroacetamideAusbeute 14,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 714019492-Methylpropan-2-ol--water (1/1)Lösungsmittel

Versuchsvorschrift

To the solution of ((N-[(1S,2R)-2-(4-Azido-phenyl)-1-fluoromethyl-2-hydroxy-ethyl]-2,2-dichloro-acetamide (150 mg, 0.465 mmol) in tert-butylalcohol:water (1:1, 3 mL) is added Na-ascorbate (12 mg, 0.060 mmol), CuSO4.5H2O (3 mg, 0.012 mmol), propargyl amine (26 mg, 0.472 mmol) resulting reaction mixture stirred at room temperature for 16 hours. Solvent is evaporated in vacuo to get the crude material purified by column chromatography eluting in 25-40% methanol in dichloromethane and washed with diethyl ether and dried under vacuum to afford the title compound (25 mg). 1H-NMR (400 MHz, DMSO-d6) δ: 3.84 (s, 2H), 4.23-4.29 (m, 1H), 4.30-4.34 (m, 0.5H), 4.42-4.46 (m, 0.5H), 4.58-4.61 (m, 0.5H), 4.69-4.73 (m, 0.5H), 4.93 (bs, 1H), 6.07 (d, 1H, J=4.28 Hz), 6.49 (s, 1H), 7.54 (d, 2H, J=8.48 Hz), 7.81 (d, 2H, J=8.52 Hz), 8.57 (s, 1H), 8.61 (d, 1H, J=5.6 Hz). LC-MS (m/z): [M+H]=376.2.

Aufarbeitung

  1. customresulting
  2. customreaction mixture
  3. customSolvent is evaporated in vacuo
  4. customto get the crude material
  5. custompurified by column chromatography
  6. washeluting in 25-40% methanol in dichloromethane
  7. washwashed with diethyl ether
  8. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-970db644a0934d4fb74563db5647cf3b
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073894B2

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