Potassium Carbonate → (2S,5S)-2-(9-Bromo-8-oxo-8,9,10,11-tetrahydro-5H-dibenzo[c,g]chromen-3-yl)-2-oxoethyl 1-((2S,3S)-2-(methoxycarbonylamino)-3-methylpentanoyl)-5-methylpyrrolidine-2-carboxylate

HRID 590676Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 590676
[Br:1][CH:2]1[CH2:23][CH2:22][C:5]2=[CH:6][C:7]3[C:8]4[CH:17]=[CH:16][C:15]([C:18](=[O:21])[CH2:19]Br)=[CH:14][C:9]=4[CH2:10][O:11][C:12]=3[CH:13]=[C:4]2[C:3]1=[O:24].[CH3:25][O:26][C:27]([NH:29][C@@H:30]([C@@H:42]([CH3:45])[CH2:43][CH3:44])[C:31]([N:33]1[C@@H:37]([CH3:38])[CH2:36][CH2:35][C@H:34]1[C:39]([OH:41])=[O:40])=[O:32])=[O:28].C([O-])([O-])=O.[K+].[K+]>ClCCl>[CH3:25][O:26][C:27]([NH:29][C@@H:30]([C@@H:42]([CH3:45])[CH2:43][CH3:44])[C:31]([N:33]1[C@@H:37]([CH3:38])[CH2:36][CH2:35][C@H:34]1[C:39]([O:41][CH2:19][C:18]([C:15]1[CH:16]=[CH:17][C:8]2[C:7]3[CH:6]=[C:5]4[CH2:22][CH2:23][CH:2]([Br:1])[C:3](=[O:24])[C:4]4=[CH:13][C:12]=3[O:11][CH2:10][C:9]=2[CH:14]=1)=[O:21])=[O:40])=[O:32])=[O:28]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 866883729-bromo-3-(2-bromoacetyl)-10,11-dihydro-5H-dibenzo[c,g]chromen-8(9H)-oneHCID 86723610(2S,5S)-1-((2S,3S)-2-(methoxycarbonylamino)-3-methylpentanoyl)-5-methylpyrrolidine-2-carboxylic acid

Produkt 1

HCID 86723609(2S,5S)-2-(9-Bromo-8-oxo-8,9,10,11-tetrahydro-5H-dibenzo[c,g]chromen-3-yl)-2-oxoethyl 1-((2S,3S)-2-(methoxycarbonylamino)-3-methylpentanoyl)-5-methylpyrrolidine-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a slurry of 9-bromo-3-(2-bromoacetyl)-10,11-dihydro-5H-dibenzo[c,g]chromen-8(9H)-one (4.00 g, 8.88 mmol) in dichloromethane (50 mL) was added (2S,5S)-1-((2S,3S)-2-(methoxycarbonylamino)-3-methylpentanoyl)-5-methylpyrrolidine-2-carboxylic acid (2.80 g, 9.32 mmol) and K2CO3 (1.84 g, 13.31 mmol). The resulting slurry was stirred at room temperature for 18 h. The reaction was diluted with dichloromethane and washed with aqueous HCl (0.5 M) and Brine. The aqueous layers were back extracted with dichloromethane (2×), and the combined organic layers were dried over Na2SO4 and concentrated. The crude product was taken directly into the next reaction.

Aufarbeitung

  1. washwashed with aqueous HCl (0.5 M) and Brine
  2. extractionThe aqueous layers were back extracted with dichloromethane (2×)
  3. dry with materialthe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude product was taken directly into the next reaction

Quellen und Nachweise

ORD-Eintrag
ord-e20f73d7ea044d97840e7a0c327a4533
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09233974B2

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