Triethylamine → N-[(2'-(triphenylmethyltetrazol-5-yl)biphenyl-4-yl) methyl]-phenylalanine t-butyl ester

HRID 257116Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 257116
Cl.[C:2]([O:6][C:7](=[O:17])[C@H:8]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[NH2:9])([CH3:5])([CH3:4])[CH3:3].[C:18]1([C:24]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[N:25]2[C:29]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[C:36]3[CH:41]=[CH:40][C:39]([CH2:42]Br)=[CH:38][CH:37]=3)=[N:28][N:27]=[N:26]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(N(CC)CC)C>C(OCC)(=O)C>[C:2]([O:6][C:7](=[O:17])[C@H:8]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[NH:9][CH2:42][C:39]1[CH:38]=[CH:37][C:36]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2[C:29]2[N:25]([C:24]([C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)([C:44]3[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=3)[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:26]=[N:27][N:28]=2)=[CH:41][CH:40]=1)([CH3:5])([CH3:3])[CH3:4]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 100534615-(4'-(Bromomethyl)(1,1'-biphenyl)-2-yl)-1-trityl-1H-tetraazoleHCID 11459563L-Phenylalanine, 1,1-dimethylethyl ester, hydrochloride (1:1)

Produkt 1

HCID 54189989N-[(2'-(triphenylmethyltetrazol-5-yl)biphenyl-4-yl) methyl]-phenylalanine t-butyl esterAusbeute 25 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

L-phenylalanine t-butyl ester hydrochloride (Bachem Bioscience, Inc.) (1.0 g, 3.9 mmol) was suspended in ethyl acetate, washed with saturated NaHCO3 and brine, dried (MgSO4), filtered and the solvent removed in vacuo. This residue was dissolved in 20 mL of THF and 1.95 g (3.5 mmol) of 2'-(N-triphenylmethyl tetrazol-5-yl)-4-bromomethylbiphenyl (prepared as described in EP 0 324 377) and 0.54 mL (3.9 mmol) triethylamine were added. The reaction was stirred at room temperature for 5 days. The THF was removed in vacuo and the residue dissolved in ethyl acetate. This was extracted 3× with K2CO3 and 1× with brine, dried over (MgSO4), filtered, and the solvent removed in vacuo. The product was purified by silica gel chromatography eluting with ethyl acetate-hexanes to yield 0.61 g (25%) of a white glass.

Aufarbeitung

  1. washwashed with saturated NaHCO3 and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customthe solvent removed in vacuo
  5. dissolutionThis residue was dissolved in 20 mL of THF
  6. customThe THF was removed in vacuo
  7. dissolutionthe residue dissolved in ethyl acetate
  8. extractionThis was extracted 3× with K2CO3 and 1× with brine
  9. dry with materialdried over (MgSO4)
  10. filtrationfiltered
  11. customthe solvent removed in vacuo
  12. customThe product was purified by silica gel chromatography
  13. washeluting with ethyl acetate-hexanes

Quellen und Nachweise

ORD-Eintrag
ord-c26536f89f5f4853a471d34e0f6d20f5
Quelldatensatz
uspto-grants-1993_11
Patentnummer
US05260325

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