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Diisopropylamine → Telaprevir, (alpha-ketoamide bond reduced)-

HRID 391493
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 391493
[NH2:1][C@@H:2]([CH2:11][CH2:12][CH3:13])[CH:3]([OH:10])[C:4]([NH:6][CH:7]1[CH2:9][CH2:8]1)=[O:5].CCN=C=NCCCN(C)C.ON1C(=O)CCC1=O.[CH:33]1([C@H:39]([NH:61][C:62]([C:64]2[CH:69]=[N:68][CH:67]=[CH:66][N:65]=2)=[O:63])[C:40]([NH:42][C@@H:43]([C:57]([CH3:60])([CH3:59])[CH3:58])[C:44]([N:46]2[CH2:50][C@@H:49]3[CH2:51][CH2:52][CH2:53][C@@H:48]3[C@H:47]2[C:54](O)=[O:55])=[O:45])=[O:41])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1.C(NC(C)C)(C)C.O.ON1C2C=CC=CC=2N=N1.Cl.N[C@@H](CCC)C(O)C(NC1CC1)=O>CN(C=O)C.C(OCC)(=O)C>[CH:33]1([C@H:39]([NH:61][C:62]([C:64]2[CH:69]=[N:68][CH:67]=[CH:66][N:65]=2)=[O:63])[C:40]([NH:42][C@@H:43]([C:57]([CH3:60])([CH3:59])[CH3:58])[C:44]([N:46]2[CH2:50][C@@H:49]3[CH2:51][CH2:52][CH2:53][C@@H:48]3[C@H:47]2[C:54]([NH:1][C@@H:2]([CH2:11][CH2:12][CH3:13])[CH:3]([OH:10])[C:4]([NH:6][CH:7]2[CH2:8][CH2:9]2)=[O:5])=[O:55])=[O:45])=[O:41])[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

10

Edukt 7

HCID 7912DiisopropylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide2×HCID 80170N-HydroxysuccinimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 23634852(1S,3aR,6aS)-(2S)-2-Cyclohexyl-N-(2-pyrazinylcarbonyl)glycyl-3-methyl-L-valyloctahydrocyclopenta(c)pyrrole-1-carboxylic acid
HCID 23634853
(3S)-3-Amino-N-cyclopropyl-2-hydroxyhexanamide
HCID 66656935Hexanamide, 3-amino-N-cyclopropyl-2-hydroxy-, hydrochloride (1:1), (3S)-

Produkt 1

HCID 23634854Telaprevir, (alpha-ketoamide bond reduced)-

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The title compound is prepared from the hydroxy-amino amide product of Step g by condensation with the appropriate acid in the presence of a coupling reagent such as, e.g., EDCI and HOSu. Specifically, in a flask containing 1.2 eq. of (1S,3aR,6aS)-2-((S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoyl)octahydrocyclopenta[c]pyrrole-1-carboxylic acid (1.59 g) in 20 mL of DMF, is added 2.5 eq. of diisopropylamine (980 uL), 1.2 eq. N-hydroxybenzotriazole hydrate (411 mg) and 1.3 eq. of EDCI (558 mg). After 15 minutes of stirring at the room temperature, 1.0 eq. of (3S)-3-amino-N-cyclopropyl-2-hydroxyhexanamide hydrochloride (500 mg) is added to the mixture. After another 24 hours, the reaction mixture is diluted into 400 mL of ethyl acetate. The organic phase of the mixture is washed with HCl (1N), water, saturated sodium bicarbonate solution, brine, and then dried over MgSO4. The crude product is purified by chromatography on silica (ethyl acetate 70-100% in Hexanes) to give the tile compound.

Aufarbeitung

  1. additionis added to the mixture
  2. washThe organic phase of the mixture is washed with HCl (1N), water, saturated sodium bicarbonate solution, brine
  3. dry with materialdried over MgSO4
  4. customThe crude product is purified by chromatography on silica (ethyl acetate 70-100% in Hexanes)
  5. customto give the tile compound

Quellen und Nachweise

ORD-Eintrag
ord-14f30c26ba11478ba8b90b3dbf48510c
Quelldatensatz
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08383858B2

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