Benzenesulfonic acid, 3-amino-5-chloro-4-methyl- → N5-(3-chloro-2-methyl-5-sulfophenyl)-L-glutamine

HRID 330862

Reaktionsgleichung

Reaktionsgleichung von HRID 330862
CCN(C(C)C)C(C)C.[NH:10](C(OC(C)(C)C)=O)[C@H:11]([C:17]([O:19]C(C)(C)C)=[O:18])[CH2:12][CH2:13][C:14](=[O:16])O.Cl.[NH2:32][C:33]1[CH:34]=[C:35]([S:41]([OH:44])(=[O:43])=[O:42])[CH:36]=[C:37]([Cl:40])[C:38]=1[CH3:39].C1C=NC2N(O)N=NC=2C=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>O.C(#N)C.FC(F)(F)C(O)=O.CN(C=O)C>[Cl:40][C:37]1[C:38]([CH3:39])=[C:33]([NH:32][C:14](=[O:16])[CH2:13][CH2:12][C@@H:11]([C:17]([OH:19])=[O:18])[NH2:10])[CH:34]=[C:35]([S:41]([OH:44])(=[O:43])=[O:42])[CH:36]=1

Komponenten

9

Edukt 5

HCID 80806Benzenesulfonic acid, 3-amino-5-chloro-4-methyl-HCID 81531DiisopropylethylamineHCID 181649HOAtHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 131731743Boc-Glu-OtBu hydrochloride

Produkt 1

HCID 45275582N5-(3-chloro-2-methyl-5-sulfophenyl)-L-glutamine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittelHCID 6422Trifluoroacetic acidLösungsmittelHCID 18373917Acetonitrile--water (1/1)Lösungsmittel

Versuchsvorschrift

After 2 ml of DMF and 0.52 ml (3 mmol) of DIEA were added to 303 mg (1 mmol) of Boc-Glu-OtBu hydrochloride, 221 mg (1 mmol) of 3-amino-5-chloro-4-methylbenzenesulfonic acid, 160 mg (1.3 mmol) of HOAt and 410 mg (1.3 mmol) of HATU, the mixture was stirred at room temperature overnight. The reaction solution was diluted in water-acetonitrile and purified in accordance with the purification step A to give the protected form of the product. The protected product obtained was dissolved in 5 ml of trifluoroacetic acid and stirred for 2 hours. After the solvent was removed by distillation, the mixture was purified in accordance with the purification step A to give the title compound.

Aufarbeitung

  1. custompurified in accordance with the purification step A
  2. customto give the protected form of the product
  3. customThe protected product obtained
  4. stirringstirred for 2 hours
  5. customAfter the solvent was removed by distillation
  6. customthe mixture was purified in accordance with the purification step A

Quellen und Nachweise

ORD-Eintrag
ord-514188b64829444189e1edd87a4f6c62
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877739B2

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