1,1'-Carbonyldiimidazole → 3-acetyl-1-butyl-N-{(1S,2R)-1-(3,5-difluorobenzyl)-3-[(3-ethylbenzyl)amino]-2-hydroxypropyl}-1H-indole-6-carboxamide

HRID 14224Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 14224
[C:1]([C:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13]([OH:15])=O)=[CH:10][CH:11]=2)[N:6]([CH2:16][CH2:17][CH2:18][CH3:19])[CH:5]=1)(=[O:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:32][C@@H:33]([CH2:47][C:48]1[CH:53]=[C:52]([F:54])[CH:51]=[C:50]([F:55])[CH:49]=1)[C@H:34]([OH:46])[CH2:35][NH:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[C:40]([CH2:44][CH3:45])[CH:39]=1>ClCCl>[C:1]([C:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13]([NH:32][C@@H:33]([CH2:47][C:48]3[CH:49]=[C:50]([F:55])[CH:51]=[C:52]([F:54])[CH:53]=3)[C@H:34]([OH:46])[CH2:35][NH:36][CH2:37][C:38]3[CH:43]=[CH:42][CH:41]=[C:40]([CH2:44][CH3:45])[CH:39]=3)=[O:15])=[CH:10][CH:11]=2)[N:6]([CH2:16][CH2:17][CH2:18][CH3:19])[CH:5]=1)(=[O:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 682631,1'-CarbonyldiimidazoleHCID 210857003-acetyl-1-butyl-1H-indole-6-carboxylic acidHCID 57487282(2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-[(3-ethylbenzyl)amino]butan-2-ol

Produkt 1

HCID 575082453-acetyl-1-butyl-N-{(1S,2R)-1-(3,5-difluorobenzyl)-3-[(3-ethylbenzyl)amino]-2-hydroxypropyl}-1H-indole-6-carboxamideAusbeute 77,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

3-Acetyl-1-butyl-1H-indole-6-carboxylic acid (0.322 g) was dissolved in dichloromethane (15 mL). 1,1′-Carbonyldiimidazole was added (0.171 g). The mixture was stirred for 2 h and then a mixture of (2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-[(3-ethylbenzyl)amino]butan-2-ol (0.250 g) in dichloromethane (15 mL) was added. After stirring overnight, the mixture was partitioned between dichloromethane, water, and brine. The organic layer was dried over sodium sulfate, filtered, and concentrated. The residue was chromatographed on silica gel using MeOH/dichloromethane (4/96) to give 3-acetyl-1-butyl-N-{(1S,2R)-1-(3,5-difluorobenzyl)-3-[(3-ethylbenzyl)amino]-2-hydroxypropyl}-1H-indole-6-carboxamide (0.335 g). MS (ESI+) for C34H39F2N3O3+H1 m/z 576.30 (M+H)+.

Aufarbeitung

  1. additionwas added
  2. stirringAfter stirring overnight
  3. customthe mixture was partitioned between dichloromethane, water, and brine
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-3e55af888bed43239d72fd09885e2e11
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07727997B2

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