HCID 89498794, compound → HCID 86680951, compound

HRID 1852355Notes

Reaction equation

HRID 1852355 reaction equation
[O:1]1[CH2:6][CH2:5][O:4][C:3]2[CH:7]=[C:8]([C@@H:11]([OH:30])[C@H:12]([N:19](C(C3C=CC=CC=3)CO)[CH3:20])[CH2:13][N:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)[CH:9]=[CH:10][C:2]1=2>CO.Cl.[Pd]>[O:1]1[CH2:6][CH2:5][O:4][C:3]2[CH:7]=[C:8]([C@@H:11]([OH:30])[C@H:12]([NH:19][CH3:20])[CH2:13][N:14]3[CH2:15][CH2:16][CH2:17][CH2:18]3)[CH:9]=[CH:10][C:2]1=2

Participants

5

Reactant 1

HCID 89498794HCID 89498794, compound

Product 1

HCID 86680951HCID 86680951, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of compound 4 (0.22 g, 0.468 mmol) in methanol 20 mL and 1 N HCl (5 mL) was added palladium (10%) on carbon (0.08 g, 0.752 mmol) (Degussa wet catalyst). The flask was attached to a Parr 3911 hydrogenation apparatus, evacuated via a water aspirator, and filled with H2 (40 psi). After shaking for 18 hours at room temperature, the mixture was filtered through celite with MeOH eluent. The celite pad then was washed with methanol (2×) and 2 M NH3 in dioxane (2×). The filtrate was concentrated, diluted with water, and washed with EtOAc (1×). The aq layer was made basic with satd. aq. NaHCO3 and extracted with CH2Cl2(2×) and EtOAc (3×). The combined layers were dried over MgSO4, concentrated to an oil, and used without further purification. HPLC purity 89% (tR=4.88 min). NMR (500 MHz, CDCl3) δ 6.9 (s, 1H), 6.7-6.8 (m, 2H), 4.6 (d, 1H), 4.3 (s, 4H), 2.8-2.9 (m, 1H), 2.4-2.5 (m, 6H), 2.4 (m, 3H), 1.7-1.8 (m, 5H). ESI-MS m/z 293.1 (M+H+).

Workup

  1. customevacuated via a water aspirator
  2. additionfilled with H2 (40 psi)
  3. filtrationthe mixture was filtered through celite with MeOH eluent
  4. washThe celite pad then was washed with methanol (2×) and 2 M NH3 in dioxane (2×)
  5. concentrationThe filtrate was concentrated
  6. additiondiluted with water
  7. washwashed with EtOAc (1×)
  8. extractionaq. NaHCO3 and extracted with CH2Cl2(2×) and EtOAc (3×)
  9. dry with materialThe combined layers were dried over MgSO4
  10. concentrationconcentrated to an oil
  11. customused without further purification

Sources & evidence

ORD record
ord-b4ddf6cef227454b8b81d5789169ad73
Source dataset
uspto-grants-2015_02
Patent number
US08961959B2

Reaction notes

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