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Diisopropylethylamine → Methyl 2-((s)-1-((s)-2-(benzyloxycarbonylamino)-3-(4-hydroxyphenyl)propanamido)-2-methylpropyl)-5-(7-bromo-1h-indol-3-yl)oxazole-4-carboxylate

HRID 494378
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 494378
C(N(C(C)C)CC)(C)C.Br.[NH2:11][C@H:12]([C:16]1[O:17][C:18]([C:25]2[C:33]3[C:28](=[C:29]([Br:34])[CH:30]=[CH:31][CH:32]=3)[NH:27][CH:26]=2)=[C:19]([C:21]([O:23][CH3:24])=[O:22])[N:20]=1)[CH:13]([CH3:15])[CH3:14].[C:35]([NH:45][C@H:46]([C:55](O)=[O:56])[CH2:47][C:48]1[CH:53]=[CH:52][C:51]([OH:54])=[CH:50][CH:49]=1)([O:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:36].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C([O-])(O)=O.[Na+]>CN(C)C=O>[CH2:38]([O:37][C:35]([NH:45][C@@H:46]([CH2:47][C:48]1[CH:53]=[CH:52][C:51]([OH:54])=[CH:50][CH:49]=1)[C:55]([NH:11][C@H:12]([C:16]1[O:17][C:18]([C:25]2[C:33]3[C:28](=[C:29]([Br:34])[CH:30]=[CH:31][CH:32]=3)[NH:27][CH:26]=2)=[C:19]([C:21]([O:23][CH3:24])=[O:22])[N:20]=1)[CH:13]([CH3:15])[CH3:14])=[O:56])=[O:36])[C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 712438N-benzyloxycarbonyl-l-tyrosineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 66889567methyl 2-((S)-1-amino-2-methylpropyl)-5-(7-bromo-1H-indol-3-yl)oxazole-4-carboxylate hydrobromide

Produkt 1

HCID 59595033
Methyl 2-((s)-1-((s)-2-(benzyloxycarbonylamino)-3-(4-hydroxyphenyl)propanamido)-2-methylpropyl)-5-(7-bromo-1h-indol-3-yl)oxazole-4-carboxylate
Ausbeute 107,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To diisopropylethylamine (225 mL, 1,290 mmol) stirred at 0° C. was added a solution of the title compound of Example 6 (277.5 g, 586.5 mmol), Cbz-L-tyrosine (194.2 g 615.9 mmol) and TBTU (207.2 g, 1.1 eq) in dimethylformamide (anhydrous, 2.77 L). The reaction was allowed to warm to room temperature and stirred for 16 hours at which time HPLC indicated completion of reaction. The reaction solution was slowly poured into saturated aqueous NaHCO3 (12.0 L) and stirred for 30 min. The precipitate was filtered and the filter cake was thoroughly washed with water. The resulting brown material was dried to constant mass in a vacuum oven at 40° C. to yield the title compound (435 g). The title compound was further purified by recrystallization. The title compound was dissolved in isopropanol (9.0 L) at 70° C. The insoluble material was removed by filtration and the filtrate was heated while slowly adding hexanes (9.0 L). The suspension was allowed to cool to room temperature at which time an ice bath was applied. Once cooled the mixture was stirred at ice bath temperature for 30 min and filtered. The solid was washed with hexanes and dried to constant mass at 40° C. in a vacuum oven giving pure title compound (264 g, 61% yield). 1H NMR (CDCl3): consistent with proposed structure.

Aufarbeitung

  1. customcompletion of reaction
  2. stirringstirred for 30 min
  3. filtrationThe precipitate was filtered
  4. washthe filter cake was thoroughly washed with water
  5. customThe resulting brown material was dried to constant mass in a vacuum oven at 40° C.

Quellen und Nachweise

ORD-Eintrag
ord-df75e5103f684673ab1a6e05b5bbda3f
Quelldatensatz
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07538129B2

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