Salicylic Acid → Benzyl 3-(2-hydroxybenzamido)butan-2-ylcarbamate

HRID 919148

Reaktionsgleichung

Reaktionsgleichung von HRID 919148
[NH2:1][CH:2]([CH3:16])[CH:3]([NH:5][C:6](=[O:15])[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:4].[OH:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20](O)=[O:21].N1C=CN=C1.C1CCC(N=C=NC2CCCCC2)CC1>CCOC(C)=O>[OH:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20]([NH:1][CH:2]([CH3:16])[CH:3]([NH:5][C:6](=[O:15])[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:4])=[O:21]

Komponenten

6

Edukt 4

HCID 338Salicylic AcidHCID 795ImidazoleHCID 10868DicyclohexylcarbodiimideHCID 59193262Benzyl 3-aminobutan-2-ylcarbamate

Produkt 1

HCID 67174902Benzyl 3-(2-hydroxybenzamido)butan-2-ylcarbamateAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

To a mixture of benzyl 3-aminobutan-2-ylcarbamate (5.3 g, 23.8 mmol), 2-hydroxybenzoic acid (3.28 g, 23.8 mmol) and imidazole (1.62 g, 23.8 mmol) in EtOAc (180 mL) at 0° C. was slowly added a solution of DCC (4.90 g, 23.8 mmol) in EtOAc (20 mL). The reaction mixture was stirred (RT, 16 h), filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel, eluting with PE-EA (5:1) to afford benzyl 3-(2-hydroxybenzamido)butan-2-ylcarbamate (3.2 g, 40%) as a colorless oil. Mass calculated for C19H22N2O4=342.39. found: [M+H]+=343.2.

Aufarbeitung

  1. filtrationfiltered
  2. concentrationconcentrated under reduced pressure
  3. customThe crude product was purified by column chromatography on silica gel
  4. washeluting with PE-EA (5:1)

Quellen und Nachweise

ORD-Eintrag
ord-623a921d06204cc0b7c8b99cd313927a
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09272984B2

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