Boron trifluoride → HCID 57438344, compound

HRID 1161070Notes

Reaction equation

HRID 1161070 reaction equation
[OH:1][C:2]1[C:7]([CH:8]([CH3:10])[CH3:9])=[C:6]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([CH:19](O)[C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]4[N:27]=[N:28][NH:29][N:30]=4)[CH:21]=3)=[CH:15][CH:14]=2)[CH:5]=[CH:4][C:3]=1[C:32](=[O:34])[CH3:33].[SiH](CC)(CC)CC.B(F)(F)F>C(Cl)Cl>[OH:1][C:2]1[C:7]([CH:8]([CH3:9])[CH3:10])=[C:6]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]4[N:27]=[N:28][NH:29][N:30]=4)[CH:21]=3)=[CH:17][CH:18]=2)[CH:5]=[CH:4][C:3]=1[C:32](=[O:34])[CH3:33]

Participants

5

Reactant 3

HCID 6356Boron trifluorideHCID 12052TriethylsilaneHCID 11676931HCID 11676931, compound

Product 1

HCID 57438344HCID 57438344, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 1-[2-Hydroxy-4-(4-{hydroxy-[3-(2H-tetrazol-5-yl)-phenyl]-methyl}-benzyloxy)-3-isopropyl-phenyl]-ethanone (100 mg, 0.22 mmol) in anhydrous CH2Cl2 (5.4 mL) is added Et3SiH (281 μL, 1.76 mmol) and BF3.ether complex (56 μL, 0.44 mmol). The reaction mixture is stirred for 1.5 h. The reaction mixture is quenched into saturated aqueous NH4Cl (10 mL) and extracted with a 50% tetrahydrofuran/ethyl acetate solution (3×30 mL). The organic layers are combined, washed with brine, dried over sodium sulfatesodium sulfate, and concentrated to an oil. The residue is purified by reverse phase HPLC using a gradient of 90:10 to 20:80 (H2O/0.1% TFA):CH3CN as eluent to give the title compound (29 mg, 30%). LC-MS (m/e): 441 (M−1); 1H NMR (DMSO-d6) δ 13.1 (1H, s), 7.82-8.00 (2H, m), 7.78 (1H, d), 7.30-7.55 (6H, m), 6.72 (1H, d), 5.22 (2H, s), 4.08 (2H, s), 3.57 (1H, m), 2.57 (3H, s), 1.26 (3H, s), 1.23 (3H, s).

Workup

  1. customThe reaction mixture is quenched into saturated aqueous NH4Cl (10 mL)
  2. extractionextracted with a 50% tetrahydrofuran/ethyl acetate solution (3×30 mL)
  3. washwashed with brine
  4. dry with materialdried over sodium sulfatesodium sulfate
  5. concentrationconcentrated to an oil
  6. customThe residue is purified by reverse phase HPLC

Sources & evidence

ORD record
ord-df6e6e28b3a6410a92b0306ea06e253f
Source dataset
uspto-grants-2010_10
Patent number
US07816523B2

Reaction notes

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