4-Methylmorpholine → N-(2-((tert-butyldimethylsilyloxy)methyl)-4-methoxyphenyl)-3,3,3-trifluoropropanamide

HRID 55838

Reaktionsgleichung

Reaktionsgleichung von HRID 55838
[Si:1]([O:8][CH2:9][C:10]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:11]=1[NH2:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[F:19][C:20]([F:26])([F:25])[CH2:21][C:22](O)=[O:23].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>C(Cl)Cl>[Si:1]([O:8][CH2:9][C:10]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:11]=1[NH:12][C:22](=[O:23])[CH2:21][C:20]([F:26])([F:25])[F:19])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

Komponenten

7

Edukt 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 27779723,3,3-Trifluoropropionic acidHCID 669800812-((Tert-butyldimethylsilyloxy)methyl)-4-methoxyaniline

Produkt 1

HCID 66980120N-(2-((tert-butyldimethylsilyloxy)methyl)-4-methoxyphenyl)-3,3,3-trifluoropropanamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

A mixture of 2-((tert-butyldimethylsilyloxy) methyl)-4-methoxyaniline (14.0 g), 3,3,3-trifluoro-propionic acid (7.30 g, 57.0 mmol), EDCI (15.0 g, 76.5 mmol), HOBT (11.0 g, 80.2 mmol) and NMM (22 mL, 157 mmol) in anhydrous CH2Cl2 (200 mL) was stirred at 20° C. for 2 hours. The mixture was diluted with CH2Cl2 (100 mL), the organic layer was washed with 1M HCl (100 mL), H2O (100 mL) and brine (100 mL), dried over Na2SO4 and concentrated to give the product.

Aufarbeitung

  1. washthe organic layer was washed with 1M HCl (100 mL), H2O (100 mL) and brine (100 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customto give the product

Quellen und Nachweise

ORD-Eintrag
ord-773b12b6404c462f850499a2e177f047
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09433618B2

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