Acetonitrile → HCID 178490921, compound

HRID 1028219Notes

Reaction equation

HRID 1028219 reaction equation
C(#N)C.[N:4]1[NH:5][N:6]=[N:7][C:8]=1[CH2:9][C@H:10]1[CH2:15][CH2:14][C@H:13]([O:16][C:17](=[O:24])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:12][CH2:11]1.[CH3:25][O:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31]Cl)=[CH:29][CH:28]=1>C(N(CC)CC)C>[CH3:25][O:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31][N:6]2[N:5]=[N:4][C:8]([CH2:9][C@H:10]3[CH2:15][CH2:14][C@H:13]([O:16][C:17](=[O:24])[C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH2:12][CH2:11]3)=[N:7]2)=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 699934-Methyloxybenzyl chlorideHCID 178525706HCID 178525706, compound

Product 1

HCID 178490921HCID 178490921, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To an acetonitrile (20 mL) suspension of trans-benzoic acid 4-(2H-tetrazol-5-ylmethyl)-cyclohexyl ester (1.34 g) obtained in Example (44b), triethylamine (0.68 mL) and 4-methoxybenzyl chloride (0.70 mL) were added at room temperature. The reaction mixture was heated to reflux for 2 hours, cooled to room temperature, concentrated, then diluted with ethyl acetate, and filtered. The filtrate was washed with 1 N hydrochloric acid, then dried over sodium sulfate, and then concentrated. The residue was purified by column chromatography (hexane/ethyl acetate) to obtain the title compound (610 mg, 32%) as a colorless oil.

Workup

  1. additionwere added at room temperature
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux for 2 hours
  4. concentrationconcentrated
  5. additiondiluted with ethyl acetate
  6. filtrationfiltered
  7. washThe filtrate was washed with 1 N hydrochloric acid
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated
  10. customThe residue was purified by column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-2cef78646dc54deebf7fb3b92e65426e
Source dataset
uspto-grants-2014_05
Patent number
US08735425B2

Reaction notes

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