Pyridine → 3-[(4S)-4-amino-5-ethoxy-5-oxopentanamido]-5-chloro-2-hydroxybenzene-1-sulfonic acid

HRID 330872Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 330872
CN(C(ON1N=[N:16][C:11]2[CH:12]=[CH:13][CH:14]=[N:15][C:10]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=NC2N([OH:34])N=NC=2C=1.NC1[C:37]([OH:47])=[C:38]([S:43]([OH:46])(=[O:45])=[O:44])[CH:39]=[C:40]([Cl:42])[CH:41]=1.N1[CH:53]=[CH:52]C=CC=1.[C:54]([OH:60])(C(F)(F)F)=[O:55]>CN(C=O)C>[NH2:16][C@H:11]([C:54]([O:60][CH2:52][CH3:53])=[O:55])[CH2:12][CH2:13][C:14]([NH:15][C:10]1[C:37]([OH:47])=[C:38]([S:43]([OH:46])(=[O:44])=[O:45])[CH:39]=[C:40]([Cl:42])[CH:41]=1)=[O:34]

Komponenten

7

Edukt 5

HCID 1049PyridineHCID 6422Trifluoroacetic acidHCID 69273-Amino-5-chloro-2-hydroxybenzenesulfonic acidHCID 181649HOAtHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Produkt 1

HCID 534690273-[(4S)-4-amino-5-ethoxy-5-oxopentanamido]-5-chloro-2-hydroxybenzene-1-sulfonic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

After 92 mg (0.33 mmol) of the compound obtained in Step 1, 130 mg (0.33 mmol) of HATU, 45 mg (0.33 mmol) of HOAt and 77 mg (0.33 mmol) of 3-amino-5-chloro2-hydroxybenzenesulfonic acid were suspended in 1.0 ml of DMF, 0.25 ml of pyridine was added to the suspension. The mixture was stirred at room temperature overnight. The solvent was removed by distillation and the mixture was purified in accordance with the purification step A to give the intermediate. The crude product was dissolved in 4.0 ml of TFA. The solution was stirred at room temperature for an hour. The solvent was removed by distillation and the mixture was purified in accordance with the purification step A to give 47.2 mg of the title compound.

Aufarbeitung

  1. customThe solvent was removed by distillation
  2. customthe mixture was purified in accordance with the purification step A
  3. customto give the intermediate
  4. stirringThe solution was stirred at room temperature for an hour
  5. customThe solvent was removed by distillation
  6. customthe mixture was purified in accordance with the purification step A

Quellen und Nachweise

ORD-Eintrag
ord-64343dd915bd4ddc917e9314ddae75ac
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877739B2

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