Citric Acid → pentyl[2'-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-ylmethyl]amine

HRID 1033816Notes

Reaction equation

HRID 1033816 reaction equation
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]([C:20]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:18]=[N:17][N:16]=2)=[CH:5][CH:4]=1.[CH2:39]([NH2:44])[CH2:40][CH2:41][CH2:42][CH3:43].C(N(CC)CC)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(Cl)Cl>[CH2:39]([NH:44][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]([C:20]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:18]=[N:17][N:16]=2)=[CH:5][CH:4]=1)[CH2:40][CH2:41][CH2:42][CH3:43]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 8060PentylamineHCID 8471TriethylamineHCID 100534615-(4'-(Bromomethyl)(1,1'-biphenyl)-2-yl)-1-trityl-1H-tetraazole

Product 1

HCID 19024425pentyl[2'-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-ylmethyl]amineYield 98.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 10.0 g (16.5 mmole) of 5-[4'-(bromomethyl)biphenyl-2-yl]-N-trityltetrazole [P. E. Aldrich, M. E. Pierce, and J. J. V. Duncia, European Patent Application 291,969 (1988)], 9.5 mL (7.14 g, 8.2 mmole) of n-pentylamine, 2.8 mL (2.03 g, 20 mmole) of triethylamine, and 100 mL of dry methylene chloride was stirred under N2 at room temperature overnight. Next, the mixture was shaken with 100 mL of 0.25M citric acid (aqueous). The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. The viscous oil was flash chromatographed on silica gel (elution initially with 1:1 hexane-EtOAc and then with a larger volume of EtOAc alone) to yield 4.57 g (49%) of the title compound as a very viscous oil, homogeneous by TLC (EtOAc); FAB-MS m/e 563 (M+1)+.

Workup

  1. dry with materialThe organic layer was dried over sodium sulfate
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customchromatographed on silica gel (
  5. washelution initially with 1:1 hexane-EtOAc

Sources & evidence

ORD record
ord-496c7309adb141278be6cb72e7758e1e
Source dataset
uspto-grants-1994_05
Patent number
US05312820

Reaction notes

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