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2-Furancarboxylic acid → HCID 67331985, Verbindung

HRID 1672258
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1672258
[C:1]([O:5][C:6](=[O:33])[CH:7]([NH:17][C:18]([C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][C:29]([NH2:32])=[CH:28][CH:27]=2)=[CH:22][CH:21]=1)=[O:19])[CH2:8][CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])([CH3:4])([CH3:3])[CH3:2].[O:34]1[CH:38]=[CH:37][CH:36]=[C:35]1[C:39](O)=[O:40].CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.O>[C:1]([O:5][C:6](=[O:33])[CH:7]([NH:17][C:18]([C:20]1[CH:21]=[CH:22][C:23]([C:26]2[CH:27]=[CH:28][C:29]([NH:32][C:39]([C:35]3[O:34][CH:38]=[CH:37][CH:36]=3)=[O:40])=[CH:30][CH:31]=2)=[CH:24][CH:25]=1)=[O:19])[CH2:8][CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])([CH3:2])([CH3:3])[CH3:4]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 69192-Furancarboxylic acidHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 67333061HCID 67333061, Verbindung

Produkt 1

HCID 67331985HCID 67331985, VerbindungAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2-[(4′-Amino-biphenyl-4-carbonyl)-amino]-pentanedioic acid di-tert-butyl ester (350 mg, 0.77 mmol) and 2-Furoic acid (87 mg, 0.77 mmol, 1 equiv.) in DMF (6 mL) was added BOP reagent (409 mg, 0.92 mmol, 1.2 equiv.) and Hunig base (0.16 mL, 0.92 mmol, 1.2 equiv.) under N2. The mixture was stirred at room temperature overnight. Reaction was complete was determined by LC-MS. The reaction mixture was then poured onto cold water. Solid precipitated from the mixture was collected by filtration. The solid was then dissolved in EtOAc, washed with 1N HCl, saturated NaHCO3, and brine, and then dried over MgSO4. After removing the solvent, the solid was dried under vacuum overnight to provide 2-({4′-[(Furan-2-carbonyl)-amino]-biphenyl-4-carbonyl}-amino)-pentanedioic acid di-tert-butyl ester in 87% yield (369 mg). MS (ESI) m/z 549.

Aufarbeitung

  1. customReaction
  2. customSolid precipitated from the mixture
  3. filtrationwas collected by filtration
  4. dissolutionThe solid was then dissolved in EtOAc
  5. washwashed with 1N HCl, saturated NaHCO3, and brine
  6. dry with materialdried over MgSO4
  7. customAfter removing the solvent
  8. customthe solid was dried under vacuum overnight

Quellen und Nachweise

ORD-Eintrag
ord-4726b34873f34329bf4cbecd5b3e289d
Quelldatensatz
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07998965B2

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