Borohydride → Ethyl(4-{4-[5-(4-tert-butylphenyl)-4-methyl-4H-[1,2,4]-triazol-3-ylsulfanyl]-2-heptyloxybenzyl amino}phenyl)acetate

HRID 1171434Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1171434
[CH2:1]([O:8][C:9]1[CH:28]=[C:27](I)[CH:26]=[CH:25][C:10]=1[CH2:11][NH:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:15][CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[C:30]([C:34]1[CH:39]=[CH:38][C:37]([C:40]2[N:41]([CH3:46])[C:42]([SH:45])=[N:43][N:44]=2)=[CH:36][CH:35]=1)([CH3:33])([CH3:32])[CH3:31].[BH4-]>O1CCCC1.C(O)C>[CH2:23]([O:22][C:20](=[O:21])[CH2:19][C:16]1[CH:17]=[CH:18][C:13]([NH:12][CH2:11][C:10]2[CH:25]=[CH:26][C:27]([S:45][C:42]3[N:41]([CH3:46])[C:40]([C:37]4[CH:38]=[CH:39][C:34]([C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:35][CH:36]=4)=[N:44][N:43]=3)=[CH:28][C:9]=2[O:8][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])=[CH:14][CH:15]=1)[CH3:24]

Komponenten

6

Edukt 3

HCID 28123BorohydrideHCID 86611168Ethyl [4-(2-heptyloxy-4-iodobenzylamino)phenyl]acetateHCID 178481686HCID 178481686, Verbindung

Produkt 1

HCID 11227433Ethyl(4-{4-[5-(4-tert-butylphenyl)-4-methyl-4H-[1,2,4]-triazol-3-ylsulfanyl]-2-heptyloxybenzyl amino}phenyl)acetate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of ethyl [4-(2-heptyloxy-4-iodo benzylamino)phenyl]acetate obtained in Step d (4.11 g, 8.07 mmol) in a mixture of tetrahydrofuran (THF) (18 ml) and ethanol (18 ml) is added dropwise to a mixture of 5-(4-tert-butylphenyl)-4-methyl-4H-[1,2,4]-triazole-3-thiol (2.99 g, 12.1 mmol), bis(bipyridine)nickel (II) bromide (106 mg, 0.2 mmol) (Organometallics, 4, (1985), 657-661) and 9.68 g of borohydride polymer supported on Amberlite® IRA400 resin at 2.5 mmol/g (Aldrich) in 18 ml of a mixture of THF and ethanol 50:50. The mixture is heated for 20 hours under reflux, and then filtered at room temperature. The filtrate is concentrated using a rotary evaporator. The product is purified by chromatography on a silica column, eluted with a heptane/ethyl acetate 7:3 mixture. After evaporation of the solvents, 4.58 g (90%) of the expected compound are recovered in the form of an oil.

Aufarbeitung

  1. temperatureThe mixture is heated for 20 hours
  2. temperatureunder reflux
  3. filtrationfiltered at room temperature
  4. concentrationThe filtrate is concentrated
  5. customa rotary evaporator
  6. customThe product is purified by chromatography on a silica column
  7. washeluted with a heptane/ethyl acetate 7:3 mixture
  8. customAfter evaporation of the solvents, 4.58 g (90%) of the expected compound
  9. customare recovered in the form of an oil

Quellen und Nachweise

ORD-Eintrag
ord-fe966cb0b4b5497d85742391141660b8
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07829588B2

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