Dichloromethane → N5-(3-chloro-4-methyl-5-sulfophenyl)-L-glutamine

HRID 1468315Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1468315
C(Cl)Cl.[NH:4](C(OC(C)(C)C)=O)[C@H:5]([C:11]([O:13]C(C)(C)C)=[O:12])[CH2:6][CH2:7][C:8](=[O:10])O.Cl.C1N=CN(C(N2C=NC=C2)=O)C=1.[NH2:38][C:39]1[CH:40]=[C:41]([Cl:50])[C:42]([CH3:49])=[C:43]([S:45]([OH:48])(=[O:47])=[O:46])[CH:44]=1>FC(F)(F)C(O)=O.C1COCC1>[Cl:50][C:41]1[CH:40]=[C:39]([NH:38][C:8](=[O:10])[CH2:7][CH2:6][C@@H:5]([C:11]([OH:13])=[O:12])[NH2:4])[CH:44]=[C:43]([S:45]([OH:48])(=[O:47])=[O:46])[C:42]=1[CH3:49]

Komponenten

7

Edukt 4

HCID 6344DichloromethaneHCID 682631,1'-CarbonyldiimidazoleHCID 808054-Amino-6-chlorotoluene-2-sulphonic acidHCID 131731743Boc-Glu-OtBu hydrochloride

Produkt 1

HCID 45275785N5-(3-chloro-4-methyl-5-sulfophenyl)-L-glutamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6422Trifluoroacetic acidLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

After 1 ml of methylene chloride and 1 ml of THF were added to 303 mg (1 mmol) of Boc-Glu-OtBu hydrochloride and 180 mg (1.1 mmol) of CDI, 221 mg of 5-amino-3-chloro-2-methylbenzenesulfonic acid was further added to mixture. The mixture was stirred at room temperature overnight and then purified in accordance with the purification step A to give the protected product. The protected product obtained was dissolved in 5 ml of trifluoroacetic acid. The solution was stirred for 2 hours. The solvent was distilled off and the mixture was purified in accordance with the purification step A to give the title compound.

Aufarbeitung

  1. additionwas further added to mixture
  2. custompurified in accordance with the purification step A
  3. customto give the protected product
  4. customThe protected product obtained
  5. stirringThe solution was stirred for 2 hours
  6. distillationThe solvent was distilled off
  7. customthe mixture was purified in accordance with the purification step A

Quellen und Nachweise

ORD-Eintrag
ord-737185491c0b41f8942e5d97ae0046fa
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09000208B2

Notizen zur Reaktion

Wird geladen…