HCID 59302564, compound → HCID 46849914, compound

HRID 2237441Notes

Reaction equation

HRID 2237441 reaction equation
C(OC([N:6]1[CH2:12][CH2:11][C:10]2[C:13]([O:18][CH3:19])=[C:14]([CH2:16]O)[S:15][C:9]=2[CH2:8][CH2:7]1)=O)C>CCOC(C)=O.[Pd]>[CH3:19][O:18][C:13]1[C:10]2[CH2:11][CH2:12][NH:6][CH2:7][CH2:8][C:9]=2[S:15][C:14]=1[CH3:16]

Participants

4

Reactant 1

HCID 59302564HCID 59302564, compound

Product 1

HCID 46849914HCID 46849914, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

The product of step d) (70 mg, 0.25 mmol) was dissolved in 10 mL EtOAc and treated with 35 mg of 10% Pd/C (wet, Degussa type E101) and stirred rapidly under an atmosphere of H2 for 3 hour. The reaction was filtered and concentrated. The crude residue was dissolved in 1 mL EtOH and treated with 1 mL 40% aqueous KOH. After heating to 80° C. overnight, the reaction was diluted with water and the product was extracted 2× into DCM. The title compound was obtained upon purification by preparative HPLC-MS. 1H NMR (CDCl3) δ 3.69 (s, 3H), 3.21-3.14 (m, 4H), 3.00 (t; J=5.2 Hz, 2H), 2.88 (t, J=5.1 Hz, 2H), 2.29 (s, 3H); MS: ESI (positive): 198 (M+H).

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated
  3. dissolutionThe crude residue was dissolved in 1 mL EtOH
  4. additiontreated with 1 mL 40% aqueous KOH
  5. additionthe reaction was diluted with water
  6. extractionthe product was extracted 2× into DCM

Sources & evidence

ORD record
ord-712b714c85814621be01982c0e66eb33
Source dataset
uspto-grants-2010_05
Patent number
US07718647B2

Reaction notes

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