Hydrochloric Acid → n-((5s)-3-(4-(2s-(Pyrimidin-2-yl)thiomethyl-2,5-dihydropyrrol-4-yl)phenyl)-2-oxooxazolidin-5-ylmethyl)acetamide

HRID 395567Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 395567
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[S:7][CH2:8][CH:9]1[CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:24][C@H:23]([CH2:25][NH:26][C:27](=[O:29])[CH3:28])[O:22][C:21]3=[O:30])=[CH:16][CH:15]=2)[CH2:11][N:10]1C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.Cl.CC(C)=O.Cl>CC(C)=O.O>[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[S:7][CH2:8][CH:9]1[CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:24][C@H:23]([CH2:25][NH:26][C:27](=[O:29])[CH3:28])[O:22][C:21]3=[O:30])=[CH:16][CH:15]=2)[CH2:11][NH:10]1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 19044839Acetone hydrogen chlorideHCID 69997770n-((5s)-3-(4-(2s-(Pyrimidin-2-yl)thiomethyl-1-trityl-2,5-dihydropyrrol-4-yl)phenyl)-2-oxooxazolidin-5-ylmethyl)acetamide

Produkt 1

HCID 69998857n-((5s)-3-(4-(2s-(Pyrimidin-2-yl)thiomethyl-2,5-dihydropyrrol-4-yl)phenyl)-2-oxooxazolidin-5-ylmethyl)acetamideAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

The N-trityl compound (Example 30, 0.528 g, 0.79 mM) in acetone (8 ml) at 0° C. was treated with freshly prepared HCl/acetone (4 ml) and stirred. The mixture was periodically treated with 10% HCl in water until TLC indicated consumption of starting material. The reaction mixture was then diluted with EtOAc (30 ml) and taken to pH 11 with NH4OH solution. The aqueous layer was extracted with EtOAc and the combined organics dried (MgSO4) and evaporated to a residue which was triturated with diethyl ether to give the title amine (0.309 g, 92%) which was used without further purification.

Aufarbeitung

  1. customconsumption of starting material
  2. additionThe reaction mixture was then diluted with EtOAc (30 ml)
  3. extractionThe aqueous layer was extracted with EtOAc
  4. dry with materialthe combined organics dried (MgSO4)
  5. customevaporated to a residue which
  6. customwas triturated with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-0030985c8ff84c79b30fcf1ac4e763f2
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06605630B1

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