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Sodium borohydride → tert-Butyl 4-({6-[(2-{4-[(biphenyl-2-ylcarbamoyl)oxy]piperidin-1-yl}ethyl)(methyl)amino]-6-oxohexyl}amino)-2-methylbenzoate

HRID 446520
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 446520
[C:1]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8](=[O:28])[O:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][N:18]([CH3:27])[C:19](=[O:26])[CH2:20][CH2:21][CH2:22][CH2:23][CH:24]=O)[CH2:12][CH2:11]1.[NH2:35][C:36]1[CH:48]=[CH:47][C:39]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])=[C:38]([CH3:49])[CH:37]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[BH4-].[Na+]>C(Cl)Cl.C(O)(=O)C>[C:1]1([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]([O:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][N:18]([CH3:27])[C:19](=[O:26])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][NH:35][C:36]2[CH:48]=[CH:47][C:39]([C:40]([O:42][C:43]([CH3:44])([CH3:45])[CH3:46])=[O:41])=[C:38]([CH3:49])[CH:37]=2)[CH2:12][CH2:11]1)=[O:28]
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Komponenten

7

Edukt 4

HCID 4311764Sodium borohydrideHCID 5049666Sodium triacetoxyborohydrideHCID 45089772Tert-butyl 4-amino-2-methylbenzoateHCID 867619011-{2-[Methyl(6-oxohexanoyl)amino]ethyl}piperidin-4-yl biphenyl-2-ylcarbamate

Produkt 1

HCID 86761900tert-Butyl 4-({6-[(2-{4-[(biphenyl-2-ylcarbamoyl)oxy]piperidin-1-yl}ethyl)(methyl)amino]-6-oxohexyl}amino)-2-methylbenzoate
Ausbeute 60,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The compound (135 mg, 0.289 mmol) obtained in Example 4g and the compound (103 mg, 0.473 mmol) obtained in Example 18a were dissolved in methylene chloride (4 mL), acetic acid (73 μL) and sodium triacetoxyborohydride (137 mg, 0.645 mmol) were added, and the mixture was stirred overnight at room temperature. Sodium borohydride (16 mg, 0.430 mmol) was added, and the mixture was stirred at room temperature for 20 minutes. The solvent was evaporated under reduced pressure, and the resulting residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=1:1→1:2, v/v) to give the title compound (114 mg; yield, 40%) as a white solid.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 20 minutes
  2. customThe solvent was evaporated under reduced pressure
  3. customthe resulting residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=1:1→1:2, v/v)

Quellen und Nachweise

ORD-Eintrag
ord-f9918814954c4603a0b05f02bc18a486
Quelldatensatz
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08476253B2

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