Trifluoroacetic acid methylene chloride → HCID 67354535, Verbindung

HRID 1676602Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1676602
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:45])[C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23]3[N:24]=[CH:25][C:26]4[N:32]([CH3:33])[C:31](=[O:34])[C:30]([F:36])([F:35])[CH2:29][N:28]([CH:37]5[CH2:41][CH2:40][CH2:39][CH2:38]5)[C:27]=4[N:42]=3)=[C:18]([O:43][CH3:44])[CH:17]=2)[CH:10]([O:46][CH3:47])[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.ClCCl>ClCCl>[CH:37]1([N:28]2[CH2:29][C:30]([F:35])([F:36])[C:31](=[O:34])[N:32]([CH3:33])[C:26]3[CH:25]=[N:24][C:23]([NH:22][C:19]4[CH:20]=[CH:21][C:16]([C:15]([NH:14][CH:11]5[CH2:12][CH2:13][NH:8][CH2:9][CH:10]5[O:46][CH3:47])=[O:45])=[CH:17][C:18]=4[O:43][CH3:44])=[N:42][C:27]2=3)[CH2:41][CH2:40][CH2:39][CH2:38]1

Komponenten

4

Edukt 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 67354452HCID 67354452, Verbindung

Produkt 1

HCID 67354535HCID 67354535, VerbindungAusbeute 37,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixture of 0.050 g (0.075 mmole) of rac-(3S,4R)-4-[4-(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methoxy-benzoylamino]-3-methoxy-piperidine-1-carboxylic acid tert-butyl ester (I-56) and 1 mL of dichloromethane was added 1 mL of trifluoroacetic acid-dichloromethane (25:75). The mixture was stirred for 1.5 hours, and then concentrated under reduced pressure. The residue was dissolved in methanol, and the mixture neutralized by the addition of 1M sodium hydroxide at 0 degrees. The mixture was purified by reverse phase silica gel chromatography, eluting with acetonitrile-water (gradient, 1:99-90:10) to give 0.0156 g of rac-(3S,4R)-4-(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methoxy-N-(3-methoxy-piperidin-4-yl)-benzamide (I-57).

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in methanol
  3. additionthe mixture neutralized by the addition of 1M sodium hydroxide at 0 degrees
  4. customThe mixture was purified by reverse phase silica gel chromatography
  5. washeluting with acetonitrile-water (gradient, 1:99-90:10)

Quellen und Nachweise

ORD-Eintrag
ord-6fcb945a5d734769b5f20deef5dd51ab
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08003785B2

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