1-Hydroxybenzotriazole → HCID 67443424, Verbindung

HRID 576564

Reaktionsgleichung

Reaktionsgleichung von HRID 576564
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][NH:14][S:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[N+:24]([O-:26])=[O:25])(=[O:17])=[O:16])[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[CH2:49]([O:51][C:52](=[O:56])[CH2:53][NH:54][CH3:55])[CH3:50]>CN(C=O)C.C(Cl)(Cl)Cl>[CH2:49]([O:51][C:52](=[O:56])[CH2:53][N:54]([C:10](=[O:11])[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])[CH2:13][NH:14][S:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[N+:24]([O-:26])=[O:25])(=[O:16])=[O:17])[CH3:55])[CH3:50]

Komponenten

7

Edukt 4

HCID 757711-HydroxybenzotriazoleHCID 95849Glycine, N-methyl-, ethyl esterHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57775887(S)-2-tert-Butoxycarbonylamino-3-(2-nitro-benzenesulfonylamino)-propionic acid

Produkt 1

HCID 67443424HCID 67443424, VerbindungAusbeute 91,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

To a solution of compound A (10.0 g, 25.7 mmol) in DMF (100 mL) was added HOBt (5.2 g, 38.5 mmol) and the reaction mixture was cooled to −10° C. To this reaction mixture, EDC-HCl (5.4 g, 28.2 mmol) was added in portions over 10 min and stirred at −10° C. for 20 min. To the reaction mixture, Sarcosine ethyl ester (256.8 mmol) in CHCl3 (300 mL) was added drop wise over 30 min. The reaction mixture was stirred at this temperature for 30 min followed by stirring at ambient temperature overnight. Solvents were then removed in vacuo, and the residue was dissolved in EtOAc (500 mL), washed with water (3×300 mL), saturated aqueous NaHCO3 (2×300 mL) and brine (100 mL). The organic layer was separated, dried over Na2SO4 and concentrated in vacuo to afford compound B (11.5 g, 91%) as a cream solid. LC-MS [M+H] 489.5 (C19H28N4O9S+H, calc: 489.3). Purity >95% (UV/254 nm). Compound B was used without further purification.

Aufarbeitung

  1. stirringThe reaction mixture was stirred at this temperature for 30 min
  2. stirringby stirring at ambient temperature overnight
  3. customSolvents were then removed in vacuo
  4. dissolutionthe residue was dissolved in EtOAc (500 mL)
  5. washwashed with water (3×300 mL), saturated aqueous NaHCO3 (2×300 mL) and brine (100 mL)
  6. customThe organic layer was separated
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-de4fe0e135664b14b641eeb7687d510c
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040032B2

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