Acetonitrile → methyl 2-((tert-butoxycarbonyl)((2'-(1-(4-methoxybenzyl)-1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)amino)-3-nitrobenzoate

HRID 41795

Reaktionsgleichung

Reaktionsgleichung von HRID 41795
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]2[N:19]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)[N:18]=[N:17][N:16]=2)=[CH:5][CH:4]=1.C(#N)C.[C:32]([O:36][C:37]([NH:39][C:40]1[C:49]([N+:50]([O-:52])=[O:51])=[CH:48][CH:47]=[CH:46][C:41]=1[C:42]([O:44][CH3:45])=[O:43])=[O:38])([CH3:35])([CH3:34])[CH3:33].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:32]([O:36][C:37]([N:39]([C:40]1[C:49]([N+:50]([O-:52])=[O:51])=[CH:48][CH:47]=[CH:46][C:41]=1[C:42]([O:44][CH3:45])=[O:43])[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]2[N:19]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)[N:18]=[N:17][N:16]=2)=[CH:5][CH:4]=1)=[O:38])([CH3:35])([CH3:33])[CH3:34]

Komponenten

6

Edukt 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 9965968Methyl 2-((tert-butoxycarbonyl)amino)-3-nitrobenzoate2×HCID 529505401H-Tetrazole, 5-[4'-(bromomethyl)[1,1'-biphenyl]-2-yl]-1-[(4-methoxyphenyl)methyl]-2×

Produkt 1

HCID 70664089methyl 2-((tert-butoxycarbonyl)((2'-(1-(4-methoxybenzyl)-1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)amino)-3-nitrobenzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21584019Toluene ethylacetateLösungsmittel

Versuchsvorschrift

A mixture of 5-[4′-(bromomethyl)biphenyl-2-yl]-1-(p-methoxybenzyl)-1H-tetrazole (compound 5a, 9.25 g, 21.2 mmol), acetonitrile (107 ml), methyl 2-(tert-butoxycarbonylamino)-3-nitrobenzoate (compound 19a, 6.43 g, 21.7 mmol) and potassium carbonate (3.00 g, 21.7 mmol) was heated under reflux for 6 hr under a nitrogen atmosphere. The reaction was monitored by TLC (eluent: toluene/ethyl acetate (4:1)). The reaction mixture was cooled, and filtered, and the cake was washed with acetonitrile (35 mL). The filtrate was concentrated under reduced pressure at 35° C. or lower to give a crude product. The crude product was purified by silica gel column chromatography (eluent: toluene/ethyl acetate (100:0-4:1)), and the fraction was concentrated. To the residue was added chloroform (about 30 ml), and the mixture was concentrated. The operations were repeated four times. The residue was dried under reduced pressure in a bath at 40° C. to give methyl 2-(N-tert-butoxycarbonyl-N-{(2′-[1-(p-methoxybenzyl)-1H-tetrazol-5-yl]biphenyl-4-yl)methyl}amino)-3-nitrobenzoate (compound 20a) as a yellowish brown amorphous solid (9.83 g (71.1%)).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 6 hr under a nitrogen atmosphere
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. washthe cake was washed with acetonitrile (35 mL)
  6. concentrationThe filtrate was concentrated under reduced pressure at 35° C.
  7. customlower to give a crude product
  8. customThe crude product was purified by silica gel column chromatography (eluent: toluene/ethyl acetate (100:0-4:1))
  9. concentrationthe fraction was concentrated
  10. additionTo the residue was added chloroform (about 30 ml)
  11. concentrationthe mixture was concentrated
  12. customThe residue was dried under reduced pressure in a bath at 40° C.

Quellen und Nachweise

ORD-Eintrag
ord-701a9bd0582d4b59bcee3196b82aab71
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530506B2

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