HCID 58375206, compound → HCID 67344445, compound

HRID 536695Notes

Reaction equation

HRID 536695 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([N:12]3[CH2:19][CH2:18][C@:17]4([CH3:23])[C:20]([CH3:22])([CH3:21])[C@H:13]3[CH2:14][C:15]3[CH:27]=[CH:26][C:25]([C:28](=[O:30])[CH3:29])=[CH:24][C:16]=34)=[O:11])=[CH:9][C:4]=2[NH:3][CH:2]=1.[CH3:31][Mg]I>O1CCCC1>[N:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([N:12]3[CH2:19][CH2:18][C@:17]4([CH3:23])[C:20]([CH3:22])([CH3:21])[C@H:13]3[CH2:14][C:15]3[CH:27]=[CH:26][C:25]([C:28]([OH:30])([CH3:31])[CH3:29])=[CH:24][C:16]=34)=[O:11])=[CH:9][C:4]=2[NH:3][CH:2]=1

Participants

4

Reactant 2

HCID 58375206HCID 58375206, compoundHCID 178418373HCID 178418373, compound

Product 1

HCID 67344445HCID 67344445, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 1-[(2R,6S)-3-(3H-benzoimidazole-5-carbonyl)-6,11,11-trimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-8-yl]-ethanone (0.10 g) in tetrahydrofuran (1 mL) is added to a solution of MeMgI (3 mol/L in Et2O, 0.25 mL) in tetrahydrofuran (1 mL) chilled in an ice bath (ca. 0° C.). Then, the cooling bath is removed and the solution is stirred at room temperature. After 5 h of stirring, more MeMgI (3 mol/L in Et2O, 0.25 mL) is added and the solution is stirred at 50° C. for 4 h. After cooling in an ice bath, aqueous NH4Cl solution is added and the resulting mixture is extracted with ethyl acetate. The combined organic extracts are dried (MgSO4) and the solvent is removed under reduced pressure. The residue is purified by HPLC on reversed phase (MeCN/H2O).

Workup

  1. customThen, the cooling bath is removed
  2. stirringAfter 5 h of stirring
  3. additionmore MeMgI (3 mol/L in Et2O, 0.25 mL) is added
  4. stirringthe solution is stirred at 50° C. for 4 h
  5. temperatureAfter cooling in an ice bath
  6. additionaqueous NH4Cl solution is added
  7. extractionthe resulting mixture is extracted with ethyl acetate
  8. dry with materialThe combined organic extracts are dried (MgSO4)
  9. customthe solvent is removed under reduced pressure
  10. customThe residue is purified by HPLC on reversed phase (MeCN/H2O)

Sources & evidence

ORD record
ord-feae9bf8180c4cdd92ef841bffd280ee
Source dataset
uspto-grants-2014_10
Patent number
US08859580B2

Reaction notes

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