HCID 90387808, compound → HCID 90388609, compound

HRID 2201745Notes

Reaction equation

HRID 2201745 reaction equation
[CH3:1][O:2][CH2:3][O:4][C@H:5]1[CH2:18][C@H:17]2[C@@H:8]([C@@H:9]3[C@@H:14]([CH2:15][CH2:16]2)[CH2:13][C@@:12]2([CH3:24])[C:19]([C:22]#[N:23])=[CH:20][CH2:21][C@@H:11]2[CH2:10]3)[CH2:7][CH2:6]1.COCO[C@H]1C[C@H]2[C@@H]([C@@H]3[C@@H](CC2)C[C@@]2(C)C(OS(C(F)(F)F)(=O)=O)=CC[C@@H]2C3)CC1>CCOC(C)=O.[Pd]>[CH3:1][O:2][CH2:3][O:4][C@H:5]1[CH2:18][C@H:17]2[C@@H:8]([C@@H:9]3[C@@H:14]([CH2:15][CH2:16]2)[CH2:13][C@@:12]2([CH3:24])[C@H:19]([C:22]#[N:23])[CH2:20][CH2:21][C@H:11]2[CH2:10]3)[CH2:7][CH2:6]1

Participants

5

Reactant 2

HCID 90387808HCID 90387808, compoundHCID 90397202HCID 90397202, compound

Product 1

HCID 90388609HCID 90388609, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of compound 49 (250 mg containing the aromatic impurity carried over from compound 48) in EtOAc (40 mL) was added Pd/C (100 mg) at room temperature. Hydrogenation was carried out under 60 psi H2. After 3 h, the pressure was released and the mixture was filtered through Celite which was washed with EtOAc (100 mL). Solvent was removed and the residue was purified by flash column chromatography (silica gel eluted with 10% EtOAc in hexanes) to give compound 50 (250 mg containing the aromatic impurity carried over from compound 48): 1H NMR (CDCl3) δ 4.64 (s, 2H), 3.85-3.80 (m, 1H), 3.34 (s, 3H), 0.83 (s, 3H); 13C NMR (CDCl3) δ 121.2, 94.3, 71.8, 54.9, 48.3, 47.9, 46.7, 44.9, 44.4, 39.7, 38.1, 37.9, 36.6, 33.8, 33.7, 30.0, 28.3, 26.3, 26.2, 23.7, 14.2.

Workup

  1. filtrationthe mixture was filtered through Celite which
  2. washwas washed with EtOAc (100 mL)
  3. customSolvent was removed
  4. customthe residue was purified by flash column chromatography (silica gel eluted with 10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-9c3655b754c64183ae6112b45ca7f6c9
Source dataset
uspto-grants-2016_06
Patent number
US09365502B2

Reaction notes

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