1-Hydroxybenzotriazole → Methyl 5-chloro-2-{[4-({[3-(furan-3-yl)phenyl]carbonyl}amino)butanoyl]amino}benzoate

HRID 1626722Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1626722
Cl.[NH2:2][CH2:3][CH2:4][CH2:5][C:6]([NH:8][C:9]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12])=[O:7].[O:20]1[CH:24]=[CH:23][C:22]([C:25]2[CH:26]=[C:27]([CH:31]=[CH:32][CH:33]=2)[C:28](O)=[O:29])=[CH:21]1.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>CN(C)C(=O)C.C(OCC)(=O)C>[Cl:19][C:16]1[CH:17]=[CH:18][C:9]([NH:8][C:6](=[O:7])[CH2:5][CH2:4][CH2:3][NH:2][C:28]([C:27]2[CH:31]=[CH:32][CH:33]=[C:25]([C:22]3[CH:23]=[CH:24][O:20][CH:21]=3)[CH:26]=2)=[O:29])=[C:10]([CH:15]=1)[C:11]([O:13][CH3:14])=[O:12]

Komponenten

7

Edukt 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 189451333-(Furan-3-yl)benzoic acidHCID 66680776Methyl 2-[(4-aminobutanoyl)amino]-5-chlorobenzoate hydrochloride

Produkt 1

HCID 66679856Methyl 5-chloro-2-{[4-({[3-(furan-3-yl)phenyl]carbonyl}amino)butanoyl]amino}benzoateAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

1.00 g (3.3 mmol) of methyl 2-[(4-aminobutanoyl)amino]-5-chlorobenzoate hydrochloride, 0.61 g (3.3 mmol) of 3-(furan-3-yl)benzoic acid, 0.75 g (3.9 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, and 0.53 g (3.9 mmol) of 1-hydroxybenzotriazole were stirred in 10 mL of N,N-dimethylacetamide (DMAc) for 2 hours. After the completion of the reaction, ethyl acetate was added, and the mixture was diluted and washed with saturated sodium bicarbonate solution and saturated saline. After the organic layer was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The obtained crude product was recrystallized using a mixed solvent of ethyl acetate and n-hexane, thereby giving 1.22 g of methyl 5-chloro-2-{[4-({[3-(furan-3-yl)phenyl]carbonyl}amino)butanoyl]amino}benzoate (yield: 85%).

Aufarbeitung

  1. additionwas added
  2. additionthe mixture was diluted
  3. washwashed with saturated sodium bicarbonate solution and saturated saline
  4. dry with materialAfter the organic layer was dried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe obtained crude product
  7. customwas recrystallized

Quellen und Nachweise

ORD-Eintrag
ord-e051d01ad0a54e3593eac4ad335dd754
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785473B2

Notizen zur Reaktion

Wird geladen…