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1,2-Dichloroethane → HCID 9912651, Verbindung

HRID 227245
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 227245
C(OC([NH:8][C@H:9]([CH2:14][C:15]1[CH:20]=[C:19]([F:21])[C:18]([F:22])=[CH:17][C:16]=1[F:23])[CH2:10][C:11]([OH:13])=O)=O)(C)(C)C.C(Cl)C[Cl:26].C1C=CC2N(O)N=NC=2C=1.Cl.[CH3:39][CH:40]1[NH:46][CH2:45][CH2:44][CH2:43][N:42]2[C:47]([C:50]([F:53])([F:52])[F:51])=[N:48][N:49]=[C:41]12>CN(C=O)C.C(=O)(O)[O-].[Na+].C(N(CC)CC)C>[ClH:26].[NH2:8][C@H:9]([CH2:14][C:15]1[CH:20]=[C:19]([F:21])[C:18]([F:22])=[CH:17][C:16]=1[F:23])[CH2:10][C:11]([N:46]1[CH2:45][CH2:44][CH2:43][N:42]2[C:47]([C:50]([F:53])([F:51])[F:52])=[N:48][N:49]=[C:41]2[CH:40]1[CH3:39])=[O:13]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 7146288(R)-3-(tert-butoxycarbonylamino)-4-(2,4,5-trifluorophenyl)butanoic acidHCID 68810792HCID 68810792, Verbindung

Produkt 1

HCID 9912651HCID 9912651, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228
Dimethylformamide
Lösungsmittel
2×
HCID 8471TriethylamineLösungsmittel
HCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

To a stirred solution of (3R)-3-[(tert-butoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid (119 mg, 0.358 mmol), EDC (82 mg, 0.430 mmol) and HOBT (58 mg, 0.430 mmol) in DMF (3 mL) at room temperature under nitrogen was added a mixture of 9-methyl-3-(trifluoromethyl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a][1,4]diazepine hydrochloride from Step G (90 mg, 0.351 mmol) and triethylamine in DMF (3 mL). The resultant mixture was stirred at ambient temperature for 4 days. Then the reaction mixture was diluted with saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and concentrated. The residue was purified by preparative thin layer chromatography (5% of 10% methanolic ammonium hydroxide in dichloromethane) to yield the N-BOC precursors of the title compound as a mixture of diastereomers. Chiral HPLC separation (ChiralCel OD column, 6% ethanol/hexane) provided the individual diastereomers, each of which was treated with 4 N hydrogen chloride in dioxane at ambient temperature for 2 h. Concentration gave the individual diastereomers of the title compound. Faster eluting diastereomer: MS 436.0 (M+1); slower eluting diastereomer: MS 436.0 (M+1).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by preparative thin layer chromatography (5% of 10% methanolic ammonium hydroxide in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-5c650bf821f54082a0135208a9ddc724
Quelldatensatz
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07560455B2

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