Trimethylsilyldiazomethane → HCID 11521576, compound

HRID 1725956Notes

Reaction equation

HRID 1725956 reaction equation
C(OC([NH:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]=1[C:19]([OH:21])=[O:20])=O)(C)(C)C.[CH3:22][Si](C=[N+]=[N-])(C)C>C1C=CC=CC=1.CO.C(O)(=O)C>[CH3:22][O:21][C:19]([C:10]1[C:11]2[CH2:12][CH2:13][CH2:14][CH2:15][C:16]=2[CH:17]=[CH:18][C:9]=1[NH2:8])=[O:20]

Participants

6

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 68863067HCID 68863067, compound

Product 1

HCID 11521576HCID 11521576, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolvent2×HCID 241BenzeneSolventHCID 887MethanolSolvent

Procedure

The white solid from Example 128B (7.17 g, 24.61 mmol) was dissolved in benzene (250 ml) and methanol (62 ml). To the stirring solution was added 2 M trimethylsilyldiazomethane (12.3 ml) until the yellow color persisted for ten minutes. The reaction was then stirred at room temperature or 1 hour. To the solution was added acetic acid until the yellow color disappeared. The solvent was then removed. The crude material (7.52 g, 24.61 mmol) was dissolved in acetic acid (100 mL) and Pt2O (3.50 g, 15.4 mmol) was added shaken in a reactor pressurized with 60 psi of H2 at 25° C. for 80 hours, filtered, and concentrated. The concentrate was treated with dichloromethane (70 mL) and TFA (12 mL) and stirred for 3 hours. The organic layer was washed with NaOH (2×250 mL) and brine (200 mL), dried (MgSO4), filtered, and concentrated to provide the desired product. MS (ESI(+)) m/e 206+H)+; 1H NMR (300 MHz, DMSO-d6) δ 6.83 (d, 1H), 6.53 (d, 1H), 5.26 (bs, 2H), 3.78 (s, 3H), 2.62 (m, 2H), 2.57 (m, 2H), 1.64 (m, 4H).

Workup

  1. waitpersisted for ten minutes
  2. customThe solvent was then removed
  3. stirringshaken in a reactor
  4. waitpressurized with 60 psi of H2 at 25° C. for 80 hours
  5. filtrationfiltered
  6. concentrationconcentrated
  7. additionThe concentrate was treated with dichloromethane (70 mL) and TFA (12 mL)
  8. stirringstirred for 3 hours
  9. washThe organic layer was washed with NaOH (2×250 mL) and brine (200 mL)
  10. dry with materialdried (MgSO4)
  11. filtrationfiltered
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-5f1b1c4146014cf795dbc5379b49f690
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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