O-(6-Chlorobenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium Tetrafluoroborate → tert-Butyl(+/-)-3-(3-(2-cyclopentyl-2-(4-((1,3-dioxoisoindolin-2-yl)methyl)phenyl)acetamido)-2-methylphenyl)propanoate

HRID 877225Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 877225
[CH:1]1([CH:6]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][N:17]3[C:25](=[O:26])[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[C:18]3=[O:27])=[CH:12][CH:11]=2)[C:7](O)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.[B-](F)(F)(F)F.CN(C(ON1N=NC2C=CC(Cl)=CC1=2)=[N+](C)C)C.[NH2:51][C:52]1[C:53]([CH3:67])=[C:54]([CH2:58][CH2:59][C:60]([O:62][C:63]([CH3:66])([CH3:65])[CH3:64])=[O:61])[CH:55]=[CH:56][CH:57]=1>CN(C=O)C.N1C=CC=CC=1>[CH:1]1([CH:6]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][N:17]3[C:18](=[O:27])[C:19]4[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=4)[C:25]3=[O:26])=[CH:12][CH:11]=2)[C:7]([NH:51][C:52]2[C:53]([CH3:67])=[C:54]([CH2:58][CH2:59][C:60]([O:62][C:63]([CH3:64])([CH3:66])[CH3:65])=[O:61])[CH:55]=[CH:56][CH:57]=2)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

6

Edukt 3

HCID 24898642O-(6-Chlorobenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium TetrafluoroborateHCID 58136304(+/-)-2-Cyclopentyl-2-(4-((1,3-dioxoisoindolin-2-yl)methyl)phenyl)acetic acidHCID 58136633Tert-butyl 3-(3-amino-2-methylphenyl)propanoate

Produkt 1

HCID 58136374tert-Butyl(+/-)-3-(3-(2-cyclopentyl-2-(4-((1,3-dioxoisoindolin-2-yl)methyl)phenyl)acetamido)-2-methylphenyl)propanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

7.5 g (20.6 mmol) of (+/−)-2-cyclopentyl-2-(4-((1,3-dioxoisoindolin-2-yl)methyl)phenyl)acetic acid were dissolved in a mixture of 170 ml of DMF and 68 ml of pyridine, and 10.2 g (26.8 mmol) of TCTU were added. After 30 min of stirring at room temperature, 4.86 g (20.6 mmol) of tert-butyl 3-(3-amino-2-methylphenyl)propanoate were added. After stirring at room temperature overnight, the reaction mixture was concentrated and the residue pre-purified by flash chromatography on silica gel (mobile phase dichloromethane/methanol 100:1). The product obtained in this manner was triturated successively with ethanol and methanol, and the solid was filtered off with suction and dried under high vacuum. This gave 8.5 g (71% of theory) of the target compound.

Aufarbeitung

  1. additionwere added
  2. stirringAfter stirring at room temperature overnight
  3. concentrationthe reaction mixture was concentrated
  4. customthe residue pre-purified by flash chromatography on silica gel (mobile phase dichloromethane/methanol 100:1)
  5. customThe product obtained in this manner
  6. customwas triturated successively with ethanol and methanol
  7. filtrationthe solid was filtered off with suction
  8. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-4f12e5a57f6f42608c1df17ea30a880a
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987256B2

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