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Ethyl Acetate → 2-bromo-9-tert-butyl-3-methoxy-14-(1,3-thiazol-5-yl)-5,6,10,11-tetrahydro-9H-[1,4]oxazocino[7',6':4,5]pyrrolo[2,1-a]isoquinolin-8(13H)-one

HRID 1971692
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1971692
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([C:15](=O)[C:16]([N:18]([C:30]([CH3:33])([CH3:32])[CH3:31])[CH2:19][CH2:20][O:21][CH2:22][C:23]#[C:24][C:25]3[S:29][CH:28]=[N:27][CH:26]=3)=[O:17])[CH:9]2C(O)=O)=[CH:4][C:3]=1[O:35][CH3:36].C([O-])(=O)C.[Na+].C(OCC)(=O)C.[NH4+].[OH-]>C(OC(=O)C)(=O)C.C(OCC)C>[Br:1][C:2]1[C:3]([O:35][CH3:36])=[CH:4][C:5]2[CH2:6][CH2:7][N:8]3[C:15]4[C:16](=[O:17])[N:18]([C:30]([CH3:31])([CH3:32])[CH3:33])[CH2:19][CH2:20][O:21][CH2:22][C:23]=4[C:24]([C:25]4[S:29][CH:28]=[N:27][CH:26]=4)=[C:9]3[C:10]=2[CH:11]=1
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Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 14923Ammonium HydroxideHCID 517045Sodium AcetateHCID 669197587-Bromo-2-(2-(tert-butyl(2-(3-(thiazol-5-yl)prop-2-ynyloxy)ethyl)amino)-2-oxoacetyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid

Produkt 1

HCID 58124817
2-bromo-9-tert-butyl-3-methoxy-14-(1,3-thiazol-5-yl)-5,6,10,11-tetrahydro-9H-[1,4]oxazocino[7',6':4,5]pyrrolo[2,1-a]isoquinolin-8(13H)-one
Ausbeute 67,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 7918Acetic AnhydrideLösungsmittel

Versuchsvorschrift

A solution of 480 mg of 11h in 7 ml of acetic anhydride and 500 mg of anhydrous sodium acetate was heated at 105° C. for 30 min. The reaction mixture was cooled and treated with 40 ml of ice-water and stirred for 1 hr at ambient temperature to break down excess anhydride. Then, 30 ml of ethyl acetate was added and the stirred mixture was treated with cold conc. aq. NH4OH, to adjust the pH of the reaction mixture to slightly basic. The materials were extracted into ethyl acetate, washed with water, dried and concentrated. The residue was passed over a short silica column, using a gradient of toluene/ethyl acetate as eluent and the purified material thus obtained was treated with diethyl ether, to give 290 mg of 11i as white crystals; Mp 219-220° C.; Rf 0.35 (toluene/ethyl acetate 1/1). MS-ESI: [M+1] 516.04, 518.05.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. extractionThe materials were extracted into ethyl acetate
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated
  6. customthe purified material thus obtained

Quellen und Nachweise

ORD-Eintrag
ord-08caf26be1914ab6888c999b1e57415d
Quelldatensatz
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08431564B2

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