Trifluoroacetic acid → 2(R)-[(3,4-methylendioxybenzyl)-(2,6-dimethyl-4-methoxybenzenesulfonyl)amino]-3-[(2-pyrrol-1-yl)phenylcarbonylamino]-propionic acid

HRID 1760816Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1760816
C([O:5][C:6](=[O:47])[C@H:7]([N:23]([CH2:37][C:38]1[CH:43]=[CH:42][C:41]2[O:44][CH2:45][O:46][C:40]=2[CH:39]=1)[S:24]([C:27]1[C:32]([CH3:33])=[CH:31][C:30]([O:34][CH3:35])=[CH:29][C:28]=1[CH3:36])(=[O:26])=[O:25])[CH2:8][NH:9][C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N:18]1[CH:22]=[CH:21][CH:20]=[CH:19]1)=[O:11])(C)(C)C.FC(F)(F)C(O)=O>FC(F)(F)C(O)=O.C(Cl)Cl>[CH2:45]1[O:44][C:41]2[CH:42]=[CH:43][C:38]([CH2:37][N:23]([S:24]([C:27]3[C:32]([CH3:33])=[CH:31][C:30]([O:34][CH3:35])=[CH:29][C:28]=3[CH3:36])(=[O:25])=[O:26])[C@H:7]([CH2:8][NH:9][C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:18]3[CH:19]=[CH:20][CH:21]=[CH:22]3)=[O:11])[C:6]([OH:47])=[O:5])=[CH:39][C:40]=2[O:46]1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 69762802tert-butyl-2(R)-[(3,4-methylendioxybenzyl)-(2,6-dimethyl-4-methoxybenzenesulfonyl)amino]-3-[(2-pyrrol-1-yl)phenylcarbonylamino]-propionate

Produkt 1

HCID 183375482(R)-[(3,4-methylendioxybenzyl)-(2,6-dimethyl-4-methoxybenzenesulfonyl)amino]-3-[(2-pyrrol-1-yl)phenylcarbonylamino]-propionic acidAusbeute 113,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21863450Trifluoroacetic acid methylene chlorideLösungsmittel

Versuchsvorschrift

A solution of tert-butyl-2(R)-[(3,4-methylendioxybenzyl)-(2,6-dimethyl-4-methoxybenzenesulfonyl)amino]-3-[(2-pyrrol-1-yl)phenylcarbonylamino]-propionate (915 mg, 1.3 mmol) in 20% trifluoracetic acid-methylene chloride (15 ml) was stirred for 1 hour. Extra trifluoroacetic acid (0.5 ml) was added and stirring continued for 1.5 hours. The material was then condensed on the rotary evaporator and the residue was taken up in toluene (40 ml) and again condensed. This procedure was repeated twice (2×40 ml toluene, to remove traces of trifluoracetic acid) to provide 2(R)-[(3,4-methylendioxybenzyl)-(2,6-dimethyl-4-methoxybenzenesulfonyl)amino]-3-[(2-pyrrol-1-yl)phenylcarbonylamino]-propionic acid as a golden tan solid (896 mg).

Aufarbeitung

  1. customcondensed
  2. customon the rotary evaporator
  3. customagain condensed
  4. custom(2×40 ml toluene, to remove traces of trifluoracetic acid)

Quellen und Nachweise

ORD-Eintrag
ord-d1cc7f1a330442bfb1f95bb60569bd98
Quelldatensatz
uspto-grants-2005_01
Patentnummer
US06844366B2

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