4-(Heptyloxy)benzoyl chloride → 4-((4-Nitrobenzamido)methyl)phenyl 4-(heptyloxy)benzoate

HRID 923528Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 923528
[OH:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][NH:7][C:8](=[O:18])[C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[CH2:21]([O:28][C:29]1[CH:37]=[CH:36][C:32]([C:33](Cl)=[O:34])=[CH:31][CH:30]=1)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]>C(Cl)Cl>[CH2:21]([O:28][C:29]1[CH:30]=[CH:31][C:32]([C:33]([O:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8](=[O:18])[C:9]3[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=3)=[CH:19][CH:20]=2)=[O:34])=[CH:36][CH:37]=1)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Komponenten

4

Edukt 2

HCID 27241824-(Heptyloxy)benzoyl chlorideHCID 12714523N-(4-hydroxybenzyl)-4-nitrobenzamide

Produkt 1

HCID 892530414-((4-Nitrobenzamido)methyl)phenyl 4-(heptyloxy)benzoateAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Prepared using General Procedure 2: To a stirring solution of N-(4-hydroxybenzyl)-4-nitrobenzamide INT-1 (647 mg, 2.38 mmol) in DCM (10 mL) at 0° C. was added TEA (1.03 mL, 7.13 mmol) followed by 4-(heptyloxy)benzoyl chloride (12.4 mL, 2.85 mmol). The suspension was sonicated until clear then diluted with DCM (50 mL) and washed with NaHCO3 (20 mL). The organic layer was concentrated and purified by chromatography (EA/hexanes) to provide 857 mg (73%) of 4-((4-nitrobenzamido)methyl)phenyl 4-(heptyloxy)benzoate INT-2. LCMS-ESI (m/z) calculated for C28H30N2O6: 490; found 491 [M+H]+, tR=3.41 min (Method 5).

Aufarbeitung

  1. customPrepared
  2. customThe suspension was sonicated until clear
  3. washwashed with NaHCO3 (20 mL)
  4. concentrationThe organic layer was concentrated
  5. custompurified by chromatography (EA/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-d14024c373c8414da7ec56315486a940
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09278910B2

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