Trifluoroacetic acid → 5-[(3-Methyl-pentanoylamino)-methyl]-thiophene-2-carboxylic acid (2-amino-phenyl)-amide

HRID 11569Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 11569
[CH3:1][CH:2]([CH2:7][CH3:8])[CH2:3][C:4]([OH:6])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.C(OC(=O)[NH:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[NH:34][C:35]([C:37]1[S:38][C:39]([CH2:42][NH2:43])=[CH:40][CH:41]=1)=[O:36])(C)(C)C.FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>C1COCC1>[NH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[NH:34][C:35]([C:37]1[S:38][C:39]([CH2:42][NH:43][C:4](=[O:6])[CH2:3][CH:2]([CH3:1])[CH2:7][CH3:8])=[CH:40][CH:41]=1)=[O:36]

Komponenten

7

Edukt 5

HCID 6422Trifluoroacetic acidHCID 77553-Methylpentanoic acidHCID 682631,1'-CarbonyldiimidazoleHCID 516892Sodium BicarbonateHCID 69655378{2-[(5-Aminomethyl-thiophene-2-carbonyl)-amino]-phenyl}-carbamic acid t-butyl ester

Produkt 1

HCID 100204565-[(3-Methyl-pentanoylamino)-methyl]-thiophene-2-carboxylic acid (2-amino-phenyl)-amideAusbeute 59,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 33.43 mg (0.288 mmol) 3-methylpentanoic acid in 1 ml THF were added 46.67 mg (0.288 mmol) 1,1′-carbonyldiimidazol. After 1 h at rt 100 mg (0.288 mmol) {2-[(5-aminomethyl-thiophene-2-carbonyl)-amino]-phenyl}-carbamic acid t-butyl ester were added and the reaction mixture was stirred for 3 h at rt. 1.7 ml trifluoroacetic acid were added and after 2 h at rt sat. aqueous NaHCO3 was added carefully and the aqueous phase was extracted three times with ethyl acetate. The combined organic phases were dried over Na2SO4. The solvent was evaporated and the residue was subjected to silica gel chromatography (ethyl acetate/heptane 6:4) to yield 59.3 mg (0.171 mmol) 5-[(3-Methyl-pentanoylamino)-methyl]-thiophene-2-carboxylic acid (2-amino-phenyl)-amide; exact MW [M+H] calc'd: 346.16; MW found [M+H]: 346.4.

Aufarbeitung

  1. additionwas added carefully
  2. extractionthe aqueous phase was extracted three times with ethyl acetate
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. customThe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-fde35acb794e44f89d09261016546ce8
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07098247B2

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