Triethylamine → HCID 19026345, compound

HRID 1033612Notes

Reaction equation

HRID 1033612 reaction equation
CCN(CC)CC.[CH2:8]([C:10]1[N:11]=[C:12]([CH2:55][CH2:56][CH3:57])[N:13]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]3[N:35]([C:36]([C:49]4[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=4)([C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)[C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[N:34]=[N:33][N:32]=3)=[CH:21][CH:20]=2)[C:14]=1[C:15]([O-:17])=[O:16])[CH3:9].[C:58](=[O:67])([O:64][CH2:65]Cl)[O:59][C:60]([CH3:63])([CH3:62])[CH3:61]>[N+](CCCC)(CCCC)(CCCC)CCCC.[I-].C1COCC1>[CH2:8]([C:10]1[N:11]=[C:12]([CH2:55][CH2:56][CH3:57])[N:13]([CH2:18][C:19]2[CH:20]=[CH:21][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]3[N:35]([C:36]([C:49]4[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=4)([C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)[C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=4)[N:34]=[N:33][N:32]=3)=[CH:23][CH:24]=2)[C:14]=1[C:15]([O:17][CH2:65][O:64][C:58]([O:59][C:60]([CH3:63])([CH3:62])[CH3:61])=[O:67])=[O:16])[CH3:9]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 13557092Chloromethyl 1,1-dimethylethyl carbonateHCID 19026360HCID 19026360, compound

Product 1

HCID 19026345HCID 19026345, compoundYield 47.6%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

0.22 mL Et3N was added to a mixture of 0.700 g 4-ethyl-2-propyl-1-[[2'-(N-triphenylmethyl(tetrazol-5-yl))biphenyl-4-yl]methyl]imidazole-5-carboxylate, 0.26 g t-butyl chloromethyl carbonate and 0.59 g n-Bu4NI in 5 mL dry THF under Ar. The reaction was stirred 6 days at room temperature and then concentrated on a rotary evaporator. The residue was partitioned between H2O and CH2Cl2, and the organic extracts dried with MgSO4. Flash chromatography using 1:1 EtOAc/petroleum ether(bp 40°-60° C.) gave 0.40 g of the title compound.

Workup

  1. concentrationconcentrated on a rotary evaporator
  2. customThe residue was partitioned between H2O and CH2Cl2
  3. dry with materialthe organic extracts dried with MgSO4

Sources & evidence

ORD record
ord-65f2041306ef4b76ade9bbb122860907
Source dataset
uspto-grants-1994_05
Patent number
US05310929

Reaction notes

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