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3-Aminobenzenesulfonic acid → 3-[(4S)-4-amino-5-methoxy-5-oxopentanamido]benzene-1-sulfonic acid

HRID 330870
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 330870
CC(OC([NH:8][C@H:9]([C:15]([O:17][CH3:18])=[O:16])[CH2:10][CH2:11][C:12]([OH:14])=O)=O)(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C1C=NC2N(O)N=NC=2C=1.[NH2:53][C:54]1[CH:55]=[C:56]([S:60]([OH:63])(=[O:62])=[O:61])[CH:57]=[CH:58][CH:59]=1>C(Cl)Cl.FC(F)(F)C(O)=O.C(N(CC)CC)C>[NH2:8][C@H:9]([C:15]([O:17][CH3:18])=[O:16])[CH2:10][CH2:11][C:12]([NH:53][C:54]1[CH:55]=[C:56]([S:60]([OH:63])(=[O:61])=[O:62])[CH:57]=[CH:58][CH:59]=1)=[O:14]
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Komponenten

8

Edukt 4

HCID 84743-Aminobenzenesulfonic acidHCID 181649HOAtHCID 7018754(4S)-4-(((tert-butoxy)carbonyl)amino)-5-methoxy-5-oxopentanoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Produkt 1

HCID 533792923-[(4S)-4-amino-5-methoxy-5-oxopentanamido]benzene-1-sulfonic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6344DichloromethaneLösungsmittelHCID 6422Trifluoroacetic acidLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

Boc-Glu-OME, 130 mg (0.5 mmol), 190 mg (0.5 mmol) of 2-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU), 70 mg (0.5 mmol) of 7-aza-1-hydroxybenzotriazole (HOAt) and 87 mg (0.5 mmol) of 3-aminobenzenesulfonic acid were suspended in 2.0 ml of methylene chloride, and 0.5 ml of triethylamine was added to the suspension. The mixture was stirred at room temperature overnight. After the solvent was removed by distillation, the purification step A was applied to give the intermediate. The crude product was dissolved in 4.0 ml of trifluoroacetic acid (TFA) and stirred at room temperature for an hour. After the solvent was removed by distillation, the purification step A was applied to give 7.4 mg of the title compound.

Aufarbeitung

  1. customAfter the solvent was removed by distillation
  2. customthe purification step A
  3. customto give the intermediate
  4. stirringstirred at room temperature for an hour
  5. customAfter the solvent was removed by distillation
  6. customthe purification step A

Quellen und Nachweise

ORD-Eintrag
ord-db182332e4ce4210a912e5dd18932d79
Quelldatensatz
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08877739B2

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