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

HRID 1431828Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1431828
[CH3:1][O:2][C:3]([NH:5][C@@H:6]([CH:40]([CH3:42])[CH3:41])[C:7]([N:9]1[C@@H:13]([CH3:14])[CH2:12][CH2:11][C@H:10]1[C:15]([O:17][CH2:18][C:19](=[O:39])[C:20]1[CH:21]=[CH:22][C:23]2[C:32]3[CH:31]=[C:30]4[CH2:33][CH2:34][CH2:35][C:36](=[O:37])[C:29]4=[CH:28][C:27]=3[O:26][CH2:25][C:24]=2[CH:38]=1)=[O:16])=[O:8])=[O:4].[Br-:43].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl.CO.Cl>[CH3:1][O:2][C:3]([NH:5][C@@H:6]([CH:40]([CH3:42])[CH3:41])[C:7]([N:9]1[C@@H:13]([CH3:14])[CH2:12][CH2:11][C@H:10]1[C:15]([O:17][CH2:18][C:19]([C:20]1[CH:21]=[CH:22][C:23]2[C:32]3[CH:31]=[C:30]4[CH2:33][CH2:34][CH:35]([Br:43])[C:36](=[O:37])[C:29]4=[CH:28][C:27]=3[O:26][CH2:25][C:24]=2[CH:38]=1)=[O:39])=[O:16])=[O:8])=[O:4]

Komponenten

6

Edukt 2

HCID 21124087Pyridiniumtribromide2×HCID 69672293(2S,5S)-2-oxo-2-(8-oxo-8,9,10,11-tetrahydro-5H-dibenzo [c,g]chromen-3-yl)ethyl 1-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)-5-methylpyrrolidine-2-carboxylate

Produkt 1

HCID 86688346(2S,5S)-2-(9-bromo-8-oxo-8,9,10,11-tetrahydro-5H-dibenzo[c,g]chromen-3-yl)-2-oxoethyl 1-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)-5-methylpyrrolidine-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidLösungsmittelHCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

(2S,5S)-2-oxo-2-(8-oxo-8,9,10,11-tetrahydro-5H-dibenzo[c,g]chromen-3-yl)ethyl 1-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)-5-methylpyrrolidine-2-carboxylate (400 mg, 0.61 mmol) was dissolved in a solution of DCM (15 mL) and MeOH (6 mL), then treated with pyridinium tribromide (409 mg, 1.28 mmol). At 2 h, an additional portion of pyridinium tribromide (40 mg) was added. After stirring at RT for another 20 min, the reaction mixture was diluted with DCM and 10% HCl, and extracted with DCM. The organic phase was dried over MgSO4, filtered and concentrated under reduced pressure and the crude material was carried on without further purification.

Aufarbeitung

  1. extractionextracted with DCM
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customthe crude material was carried on without further purification

Quellen und Nachweise

ORD-Eintrag
ord-9a3cbfa2b8d9429d9d931999b9feffb2
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08940718B2

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