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Dichloromethane → Quinoline-6-carboxylic acid (1-benzyl-2-hydroxy-3-{3-[-phenyl-1-(3-phenyl-propyl)-butylcarbamoyl]-piperidin-1-yl}-propyl)-amide

HRID 1454138
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1454138
C1([CH2:7][CH2:8][CH2:9][CH:10]([NH:20][C:21]([CH:23]2[CH2:28][CH2:27][CH2:26][N:25]([CH2:29][CH:30]([OH:40])[CH:31]([NH2:39])[CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH2:24]2)=[O:22])[CH2:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)C=CC=CC=1.[N:41]1[C:50]2[C:45](=[CH:46][C:47]([C:51]([OH:53])=O)=[CH:48][CH:49]=2)[CH:44]=[CH:43][CH:42]=1.C(N([CH2:59][CH3:60])CC)C.Cl.CN(C)[CH2:64][CH2:65][CH2:66]N=C=NCC.[CH2:73](Cl)Cl>>[CH2:32]([CH:31]([NH:39][C:51]([C:47]1[CH:46]=[C:45]2[C:50](=[CH:49][CH:48]=1)[N:41]=[CH:42][CH:43]=[CH:44]2)=[O:53])[CH:30]([OH:40])[CH2:29][N:25]1[CH2:26][CH2:27][CH2:28][CH:23]([C:21](=[O:22])[N:20]([C:60]2[CH:59]=[CH:64][CH:65]=[CH:66][CH:73]=2)[CH:10]([CH2:11][CH2:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:9][CH2:8][CH3:7])[CH2:24]1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 5

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 825716-Quinolinecarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 187274631-(3-Amino-2-hydroxy-4-phenyl-butyl)-piperidine-3-carboxylic acid [4-phenyl-1-(3-phenyl-propyl)-butyl]-amide

Produkt 1

HCID 90923382
Quinoline-6-carboxylic acid (1-benzyl-2-hydroxy-3-{3-[-phenyl-1-(3-phenyl-propyl)-butylcarbamoyl]-piperidin-1-yl}-propyl)-amide

Versuchsvorschrift

1-(3-Amino-2-hydroxy-4-phenyl-butyl)-piperidine-3-carboxylic acid [4-phenyl-1-(3-phenyl-propyl)-butyl]-amide (20) (150 mg; 0.28 mmol) is dissolved in methylene chloride (10 mL) at ambient temperature. 6-Quinolinecarboxylic acid (48 mg; 0.28 mmol), triethylamine (0.0772 mL; 0.55 mmol), and N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (58.4 mg; 0.31 mmol) are added sequentially. The mixture is stirred for 18 hours at ambient temperature then concentrated in vacuo at 30° C. The residue is diluted with ethyl acetate (100 mL) and washed successively with water (50 mL), saturated aqueous sodium bicarbonate (50 mL), and saturated brine (50 mL). The organic layer is dried over MgSO4, filtered, and concentrated in vacuo. The residue is purified via silica gel chromatography with gradient elution (2%→20% methanol in methylene chloride) affording the desired product diastereomers (70 mg) as an oil. ESMS: MH+ 697.6 (base).

Aufarbeitung

  1. concentrationthen concentrated in vacuo at 30° C
  2. additionThe residue is diluted with ethyl acetate (100 mL)
  3. washwashed successively with water (50 mL), saturated aqueous sodium bicarbonate (50 mL), and saturated brine (50 mL)
  4. dry with materialThe organic layer is dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified via silica gel chromatography with gradient elution (2%→20% methanol in methylene chloride)

Quellen und Nachweise

ORD-Eintrag
ord-8b4c393afab4475ba199108798115685
Quelldatensatz
uspto-grants-2009_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07476680B2

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