Potassium Carbonate → Tert-Butyl(2R,5R)-2-{2-[2-({(2S)-2-[(methoxycarbonyl)amino]-3,3-diphenylpropanoyl}amino)phenyl]ethyl}-5-[2-(2-nitrophenyl)vinyl]morpholine-4-carboxylate

HRID 629724Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 629724
O.[Br-].[N+:3]([C:6]1[CH:31]=[CH:30][CH:29]=[CH:28][C:7]=1[CH2:8][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O-:5])=[O:4].C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1.[CH:56]([C@H:58]1[N:63]([C:64]([O:66][C:67]([CH3:70])([CH3:69])[CH3:68])=[O:65])[CH2:62][C@@H:61]([CH2:71][CH2:72][C:73]2[CH:78]=[CH:77][CH:76]=[CH:75][C:74]=2[NH:79][C:80](=[O:100])[C@@H:81]([NH:95][C:96]([O:98][CH3:99])=[O:97])[CH:82]([C:89]2[CH:94]=[CH:93][CH:92]=[CH:91][CH:90]=2)[C:83]2[CH:88]=[CH:87][CH:86]=[CH:85][CH:84]=2)[O:60][CH2:59]1)=O>COCCOC>[CH3:99][O:98][C:96]([NH:95][C@@H:81]([CH:82]([C:83]1[CH:84]=[CH:85][CH:86]=[CH:87][CH:88]=1)[C:89]1[CH:94]=[CH:93][CH:92]=[CH:91][CH:90]=1)[C:80]([NH:79][C:74]1[CH:75]=[CH:76][CH:77]=[CH:78][C:73]=1[CH2:72][CH2:71][C@H:61]1[O:60][CH2:59][C@@H:58]([CH:56]=[CH:8][C:7]2[CH:28]=[CH:29][CH:30]=[CH:31][C:6]=2[N+:3]([O-:5])=[O:4])[N:63]([C:64]([O:66][C:67]([CH3:68])([CH3:70])[CH3:69])=[O:65])[CH2:62]1)=[O:100])=[O:97]

Komponenten

6

Edukt 4

HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 21877565(2-Nitrobenzyl)triphenylphosphonium bromide monohydrateHCID 86726317tert-butyl (2R,5S)-5-formyl-2-[2-(2-{[N-(methoxycarbonyl)-b-phenyl-L-phenylalanyl]amino}phenyl)ethyl]morpholine-4-carboxylate

Produkt 1

HCID 86726327Tert-Butyl(2R,5R)-2-{2-[2-({(2S)-2-[(methoxycarbonyl)amino]-3,3-diphenylpropanoyl}amino)phenyl]ethyl}-5-[2-(2-nitrophenyl)vinyl]morpholine-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel2×

Versuchsvorschrift

(2-Nitrobenzyl)triphenylphosphonium bromide monohydrate (1.4 equiv), potassium carbonate (2.0 equiv) and 18-crown-6 (0.1 equiv) were combined in DME (0.16 M vs aldehyde). The mixture was stirred at room temperature for 5 min. tert-Butyl(2R,5S)-5-formyl-2-{2-[2-({(2S)-2-[(methoxycarbonyl)amino]-3,3-diphenylpropanoyl}amino)phenyl]ethyl}morpholine-4-carboxylate (1.0 equiv) was dissolved in DME (0.16 M) and added to the reaction mixture. The reaction mixture was stirred at room temperature for 18 h, filtered over solka floc and concentrated. The crude product was purified using automated silica-gel flash chromatography using a solvent gradient of 0% to 100% of ethyl acetate and hexanes.

Aufarbeitung

  1. additionadded to the reaction mixture
  2. filtrationfiltered over solka floc
  3. concentrationconcentrated
  4. customThe crude product was purified

Quellen und Nachweise

ORD-Eintrag
ord-c8cbeceb6611459bb260a7a480eac056
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09315475B2

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