Dichloromethane → Biphenyl-2-ylcarbamic Acid 1-(2-{[4-(4-{[(R)-2-(tert-butyldimethyl-silanyloxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethylamino]methyl}-phenylcarbamoyl)butyl]methylcarbamoyl}ethyl)piperidin-4-yl Ester

HRID 1039836Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1039836
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([CH2:12][CH2:13][CH2:14][CH2:15][N:16]([CH3:43])[C:17]([CH2:19][CH2:20][N:21]2[CH2:26][CH2:25][CH:24]([O:27][C:28](=[O:42])[NH:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH2:23][CH2:22]2)=[O:18])=[O:11])=[CH:5][CH:4]=1)=O.C(O)(=O)C.[NH2:48][CH2:49][C@@H:50]([C:59]1[CH:68]=[CH:67][C:66]([OH:69])=[C:65]2[C:60]=1[CH:61]=[CH:62][C:63](=[O:70])[NH:64]2)[O:51][Si:52]([C:55]([CH3:58])([CH3:57])[CH3:56])([CH3:54])[CH3:53].C(Cl)Cl.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO>[C:55]([Si:52]([CH3:54])([CH3:53])[O:51][C@H:50]([C:59]1[CH:68]=[CH:67][C:66]([OH:69])=[C:65]2[C:60]=1[CH:61]=[CH:62][C:63](=[O:70])[NH:64]2)[CH2:49][NH:48][CH2:1][C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10]([CH2:12][CH2:13][CH2:14][CH2:15][N:16]([CH3:43])[C:17]([CH2:19][CH2:20][N:21]2[CH2:22][CH2:23][CH:24]([O:27][C:28](=[O:42])[NH:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)[CH2:25][CH2:26]2)=[O:18])=[O:11])=[CH:7][CH:8]=1)([CH3:58])([CH3:57])[CH3:56]

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 5049666Sodium triacetoxyborohydrideHCID 666722995-[(R)-2-amino-1-(tert-butyldimethylsilanyloxy)ethyl]-8-hydroxy-1H-quinolin-2-one acetateHCID 86646966Biphenyl-2-ylcarbamic acid 1-(2-{[4-(4-formylphenylcarbamoyl)butyl]methylcarbamoyl}ethyl)piperidin-4-yl ester

Produkt 1

HCID 86646965Biphenyl-2-ylcarbamic Acid 1-(2-{[4-(4-{[(R)-2-(tert-butyldimethyl-silanyloxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethylamino]methyl}-phenylcarbamoyl)butyl]methylcarbamoyl}ethyl)piperidin-4-yl EsterAusbeute 82,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a stirred solution of biphenyl-2-ylcarbamic acid 1-(2-{[4-(4-formyl-phenylcarbamoyl)butyl]methylcarbamoyl}ethyl)piperidin-4-yl ester (2.83 g, 4.84 mmol) and 5-[(R)-2-amino-1-(tert-butyldimethylsilanyloxy)ethyl]-8-hydroxy-1H-quinolin-2-one acetic acid salt (1.91 g, 4.84 mmol) in a 1:1 mixture of MeOH:DCM (40.0 mL, 312 mmol) was added sodium triacetoxyborohydride (3.08 g, 14.5 mmol). The reaction mixture was stirred at room temperature for 2 h and then the layers were separated. The organic layer was washed with saturated aqueous sodium bicarbonate solution, dried over sodium sulfate, filtered and concentrated under reduced pressure to give a yellow solid. The solid was purified by silica gel flash chromatography (0-30% MeOH in DCM+0.5% NH4OH) to give the title compound (3.60 g, 82% yield) as a yellow solid.

Aufarbeitung

  1. customthe layers were separated
  2. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto give a yellow solid
  7. customThe solid was purified by silica gel flash chromatography (0-30% MeOH in DCM+0.5% NH4OH)

Quellen und Nachweise

ORD-Eintrag
ord-9e0d3b93aef743f1a0043abe0738ea57
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08551978B2

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