3(RS)-[[N-[N-[N-[N-[N-[3-(tert-butoxycarbonyl)propionyl]-O-tert-butyl-L-alpha-aspartyl]-O-tert-butyl-L-alpha-glutamyl]-2-methyl-L-phenylalanyl]-3-methyl-L-valyl]-L-leucyl]amino]-5,5,5-trifluoro-2',4'-dimethyl-2-oxovaleranilide → 3(RS)-[[N-[N-[N-[N-[N-(3-carboxypropionyl)-L-alpha-aspartyl]-L-alpha-glutamyl]-2-methyl-L-phenylalanyl]-3-methyl-L-valyl]-L-leucyl]amino]-5,5,5-trifluoro-2',4'-dimethyl-2-oxovaleranilide

HRID 635622Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 635622
C([O:5][C:6]([CH2:8][CH2:9][C:10]([NH:12][C@H:13]([C:22]([NH:24][C@H:25]([C:35]([NH:37][C@H:38]([C:47]([NH:49][C@H:50]([C:55]([NH:57][C@H:58]([C:63]([NH:65][CH:66]([CH2:80][C:81]([F:84])([F:83])[F:82])[C:67](=[O:79])[C:68]([NH:70][C:71]1[CH:76]=[CH:75][C:74]([CH3:77])=[CH:73][C:72]=1[CH3:78])=[O:69])=[O:64])[CH2:59][CH:60]([CH3:62])[CH3:61])=[O:56])[C:51]([CH3:54])([CH3:53])[CH3:52])=[O:48])[CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1[CH3:46])=[O:36])[CH2:26][CH2:27][C:28](=[O:34])[O:29]C(C)(C)C)=[O:23])[CH2:14][C:15](=[O:21])[O:16]C(C)(C)C)=[O:11])=[O:7])(C)(C)C>FC(F)(F)C(O)=O.C1(C)C=CC=CC=1>[C:6]([CH2:8][CH2:9][C:10]([NH:12][C@H:13]([C:22]([NH:24][C@H:25]([C:35]([NH:37][C@H:38]([C:47]([NH:49][C@H:50]([C:55]([NH:57][C@H:58]([C:63]([NH:65][CH:66]([CH2:80][C:81]([F:82])([F:83])[F:84])[C:67](=[O:79])[C:68]([NH:70][C:71]1[CH:76]=[CH:75][C:74]([CH3:77])=[CH:73][C:72]=1[CH3:78])=[O:69])=[O:64])[CH2:59][CH:60]([CH3:62])[CH3:61])=[O:56])[C:51]([CH3:54])([CH3:53])[CH3:52])=[O:48])[CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1[CH3:46])=[O:36])[CH2:26][CH2:27][C:28](=[O:29])[OH:34])=[O:23])[CH2:14][C:15](=[O:16])[OH:21])=[O:11])([OH:7])=[O:5]

Komponenten

4

Edukt 1

HCID 206399213(RS)-[[N-[N-[N-[N-[N-[3-(tert-butoxycarbonyl)propionyl]-O-tert-butyl-L-alpha-aspartyl]-O-tert-butyl-L-alpha-glutamyl]-2-methyl-L-phenylalanyl]-3-methyl-L-valyl]-L-leucyl]amino]-5,5,5-trifluoro-2',4'-dimethyl-2-oxovaleranilide

Produkt 1

HCID 206397723(RS)-[[N-[N-[N-[N-[N-(3-carboxypropionyl)-L-alpha-aspartyl]-L-alpha-glutamyl]-2-methyl-L-phenylalanyl]-3-methyl-L-valyl]-L-leucyl]amino]-5,5,5-trifluoro-2',4'-dimethyl-2-oxovaleranilideAusbeute 67,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

50 mg (0.042 mmol) of 3(RS)-[[N-[N-[N-[N-[N-[3-(tert-butoxycarbonyl)propionyl]-O-tert-butyl-L-α-aspartyl]-O-tert-butyl-L-α-glutamyl]-2-methyl-L-phenylalanyl]-3-methyl-L-valyl]-L-leucyl]amino]-5,5,5-trifluoro-2′,4′-dimethyl-2-oxovaleranilide were dissolved in 3 ml of trifluoroacetic acid and the solution was stirred at room temperature for 30 minutes. The solution was then diluted with 10 ml of toluene and the solvent was removed by evaporation. The solid was triturated with diethyl ether to give 29 mg of 3(RS)-[[N-[N-[N-[N-[N-(3-carboxypropionyl)-L-α-aspartyl]-L-α-glutamyl]-2-methyl-L-phenylalanyl]-3-methyl-L-valyl]-L-leucyl]amino]-5,5,5-trifluoro-2′,4′-dimethyl-2-oxovaleranilide as a white solid, MS: m/e 1020.4 [M+H]+.

Aufarbeitung

  1. customthe solvent was removed by evaporation
  2. customThe solid was triturated with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-b10c1ed5b3024611a561099828865420
Quelldatensatz
uspto-grants-2001_02
Patentnummer
US06187905B1

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