Acetic Acid → 4-[3-(Tert-butoxycarbonylamino)propoxy]-7-[1-(tert-butoxycarbonyl)-5-(3-hydroxypiperidinomethyl)indol-2-yl]isoindolinone

HRID 21123

Reaktionsgleichung

Reaktionsgleichung von HRID 21123
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:21]=[CH:20][C:19]([C:22]2[N:23]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[C:24]3[C:29]([CH:30]=2)=[CH:28][C:27]([CH:31]=O)=[CH:26][CH:25]=3)=[C:18]2[C:14]=1[CH2:15][NH:16][C:17]2=[O:40])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH:41][CH:42]1[CH2:47][CH2:46][CH2:45][NH:44][CH2:43]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl>C(#N)C>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:21]=[CH:20][C:19]([C:22]2[N:23]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[C:24]3[C:29]([CH:30]=2)=[CH:28][C:27]([CH2:31][N:44]2[CH2:45][CH2:46][CH2:47][CH:42]([OH:41])[CH2:43]2)=[CH:26][CH:25]=3)=[C:18]2[C:14]=1[CH2:15][NH:16][C:17]2=[O:40])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

7

Edukt 5

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 232933-HydroxypiperidineHCID 5049666Sodium triacetoxyborohydrideHCID 866282334-[3-(Tert-butoxycarbonylamino)propoxy]-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone

Produkt 1

HCID 684908674-[3-(Tert-butoxycarbonylamino)propoxy]-7-[1-(tert-butoxycarbonyl)-5-(3-hydroxypiperidinomethyl)indol-2-yl]isoindolinoneAusbeute 34,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

In a similar manner to Step 2 of Example 147, 4-[3-(tert-butoxycarbonylamino)propoxy]-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone (104 mg, 0.188 mmol) was dissolved in acetonitrile (5.2 mL), and the solution was treated with 3-hydroxypiperidine (76.0 mg, 0.752 mmol), acetic acid (0.215 mL, 3.76 mmol) and sodium triacetoxyborohydride (160 mg, 0.752 mmol). The reaction mixture was added with 1 mol/L hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium carbonate solution and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain 4-[3-(tert-butoxycarbonylamino)propoxy]-7-[1-(tert-butoxycarbonyl)-5-(3-hydroxypiperidinomethyl)indol-2-yl]isoindolinone (40.9 mg, yield 34%).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium carbonate solution and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-aaa72b595c844ebca3a888ec0c4019c1
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745641B2

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