Diisopropylethylamine → (1-{1-[4-Cyclopentyl-6-(6-fluoro-1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carbonyl]-2,2-dimethyl-propylcarbamoyl}-ethyl)-methyl-carbamic acid benzyl ester

HRID 1949627Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1949627
[C:1]([N:11]([CH3:17])[C@H:12]([C:14]([OH:16])=O)[CH3:13])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH2:51][CH:52]([C:78]([CH3:81])([CH3:80])[CH3:79])[C:53]([N:55]1[CH2:59][CH2:58][CH:57]2[N:60]([CH:73]3[CH2:77][CH2:76][CH2:75][CH2:74]3)[CH2:61][CH:62]([C:63]3[C:71]4[C:66](=[CH:67][C:68]([F:72])=[CH:69][CH:70]=4)[NH:65][CH:64]=3)[CH:56]12)=[O:54]>CN1C(=O)CCC1.CCOC(C)=O>[CH2:4]([O:3][C:1](=[O:2])[N:11]([CH:12]([C:14](=[O:16])[NH:51][CH:52]([C:53]([N:55]1[CH2:59][CH2:58][CH:57]2[N:60]([CH:73]3[CH2:77][CH2:76][CH2:75][CH2:74]3)[CH2:61][CH:62]([C:63]3[C:71]4[C:66](=[CH:67][C:68]([F:72])=[CH:69][CH:70]=4)[NH:65][CH:64]=3)[CH:56]12)=[O:54])[C:78]([CH3:81])([CH3:80])[CH3:79])[CH3:13])[CH3:17])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 7016365Z-N-Me-Ala-OHHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 674083852-Amino-1-[4-cyclopentyl-6-(6-fluoro-1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrol-1-yl]-3,3-dimethyl-butan-1-one

Produkt 1

HCID 67408704(1-{1-[4-Cyclopentyl-6-(6-fluoro-1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carbonyl]-2,2-dimethyl-propylcarbamoyl}-ethyl)-methyl-carbamic acid benzyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution containing Cbz-N(Me)Ala-OH (116 mg, 0.5 mmol) in anhydrous NMP (5 mL) was cooled to 0° C. HATU (191 mg, 0.5 mmol) and DIPEA (148 mg, 0.7 mmol) were added followed by the addition of crude 39 (218 mg, 0.5 mmol) in anhydrous NMP (5 mL). The reaction mixture was slowly warmed to ambient temperature. After 3 h, the reaction mixture was diluted with EtOAc and washed successively with aqueous NaHCO3 and brine, dried over anhydrous Na2SO4, filtered, and concentrated to afford 300 mg of crude 40 as an amber-colored oil which was used without further purification. Mass spectrum, m/z [646.4] (M+H)+.

Aufarbeitung

  1. temperatureThe reaction mixture was slowly warmed to ambient temperature
  2. washwashed successively with aqueous NaHCO3 and brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-4864e7574fc1447ba38a0773498fae1d
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399683B2

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