HCID 11518441, compound → HCID 11496527, compound

HRID 1726013Notes

Reaction equation

HRID 1726013 reaction equation
[CH2:1]([N:3]([CH2:32][CH3:33])[CH2:4][CH2:5]/[CH:6]=[CH:7]/[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[S:14]([NH:17][C:18]1[CH:27]=[CH:26][C:25]2[CH2:24][CH2:23][CH2:22][CH2:21][C:20]=2[C:19]=1[C:28]([O:30][CH3:31])=[O:29])(=[O:16])=[O:15])[CH3:2]>CO.[Pd]>[CH2:32]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[S:14]([NH:17][C:18]1[CH:27]=[CH:26][C:25]2[CH2:24][CH2:23][CH2:22][CH2:21][C:20]=2[C:19]=1[C:28]([O:30][CH3:31])=[O:29])(=[O:15])=[O:16])[CH3:33]

Participants

4

Reactant 1

HCID 11518441HCID 11518441, compound

Product 1

HCID 11496527HCID 11496527, compoundYield 109.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of Example 529D (300 mg, 0.64 mmol) in methanol (12 mL) was hydrogenated with H2 over 90 mg (30 wt %) of 10% Pd/C. After 4.5 hours the reaction was filtered through diatomaceous earth (Celite®). The pad was washed with methanol and the filtrates were combined with those from a 50 mg scale (0.11 mmol) reaction and concentrated to provide 332 mg (94%) of the desired product. MS (ESI(+)) m/e 473 (M+H)+; 1H NMR (400 MHz, CDCl3) δ 1.00 (t, J=7.14 Hz, 6H) 1.58 (m, 2H) 1.68 (m, 6H) 2.53 (m, 6H) 2.69 (m, 4H) 2.95 (m, 2H) 3.72 (s, 3H) 6.99 (d, J=8.51 Hz, 1H) 7.05 (d, J=8.37 Hz, 1H) 7.21 (t, J=7.68 Hz, 1H) 7.30 (d, J=7.55 Hz, 1H) 7.42 (t, J=7.14 Hz, 1H) 7.85 (d, J=7.82 Hz, 1H).

Workup

  1. filtrationAfter 4.5 hours the reaction was filtered through diatomaceous earth (Celite®)
  2. washThe pad was washed with methanol
  3. customfrom a 50 mg scale (0.11 mmol) reaction
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1370ca77e37348fd8683c3fee082f0e5
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

Loading…