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Triethylamine → benzyl (3R)-4-(3-cyanophenoxy)-3-[4-(1-t-butoxycarbonyl-4-piperidyloxy)benzoylamino]butyrate

HRID 747707
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Reaktionsgleichung

Reaktionsgleichung von HRID 747707
C(O[C:6]([NH:8][C@@H:9]([CH2:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([C:29]#[N:30])[CH:24]=1)[CH2:10][C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])=[O:7])(C)(C)C.[C:31]([O:35][C:36]([N:38]1[CH2:43][CH2:42][CH:41]([O:44][C:45]2[CH:53]=[CH:52][C:48](C(O)=O)=[CH:47][CH:46]=2)[CH2:40][CH2:39]1)=[O:37])([CH3:34])([CH3:33])[CH3:32].C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>Cl.O1CCOCC1.O1CCOCC1.O>[C:29]([C:25]1[CH:24]=[C:23]([CH:28]=[CH:27][CH:26]=1)[O:22][CH2:21][C@H:9]([NH:8][C:6](=[O:7])[C:48]1[CH:47]=[CH:46][C:45]([O:44][CH:41]2[CH2:40][CH2:39][N:38]([C:36]([O:35][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:37])[CH2:43][CH2:42]2)=[CH:53][CH:52]=1)[CH2:10][C:11]([O:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:12])#[N:30]
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Komponenten

9

Edukt 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27946494-((1-(tert-Butoxycarbonyl)piperidin-4-yl)oxy)benzoic acidHCID 10960575benzyl (3R)-3-t-butoxycarbonylamino-4-(3-cyanophenoxy)butyrate

Produkt 1

HCID 86760706
benzyl (3R)-4-(3-cyanophenoxy)-3-[4-(1-t-butoxycarbonyl-4-piperidyloxy)benzoylamino]butyrate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittelHCID 204431481,4-Dioxane hydrochlorideLösungsmittel

Versuchsvorschrift

1.46 g (3.56 mmol) of benzyl (3R)-3-(t-butoxycarbonyl)amino-4-(3-cyanophenoxy)butyrate was dissolved in 10 ml of 4 N dioxane hydrochloride and 5 ml of dioxane, and the solution was stirred for 15 hours. The solvent was evaporated, and the residue was dissolved in 20 ml of dichloromethane. 1.14 g (3.56 mmol) of 4-(1-t-butoxycarbonyl-4-piperidyloxy)benzoic acid, 2.48 ml (17.8 mmol) of triethylamine, 748 mg (3.92 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 529 mg (3.92 mmol) of 1-hydroxybenzotriazole were added to the solution, and they were stirred for 16 hours. The reaction liquid was diluted with water. After the extraction with ethyl acetate, the organic layer was successively washed with water, 1 N sodium hydroxide and saturated aqueous NaCl solution, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was treated by the silica gel column chromatography to obtain the title compound.

Aufarbeitung

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in 20 ml of dichloromethane
  3. customThe reaction liquid
  4. extractionAfter the extraction with ethyl acetate
  5. washthe organic layer was successively washed with water, 1 N sodium hydroxide and saturated aqueous NaCl solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated
  8. additionthe residue was treated by the silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-e995f61667c9411aa4fbf03ee1233b57
Quelldatensatz
uspto-grants-2008_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07396844B1

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