HCID 22716444, compound → HCID 22716425, compound

HRID 1582887Notes

Reaction equation

HRID 1582887 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([O:32][CH3:33])=[CH:11][C:12]([N+:29]([O-])=O)=[C:13]([C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[CH:21]=[C:20]([O:25][CH3:26])[C:19]([O:27][CH3:28])=[CH:18]3)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(OCC)(=O)C.[Pd]>[NH2:29][C:12]1[CH:11]=[C:10]([O:32][CH3:33])[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:14][C:13]=1[C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[CH:21]=[C:20]([O:25][CH3:26])[C:19]([O:27][CH3:28])=[CH:18]2

Participants

4

Reactant 1

HCID 22716444HCID 22716444, compound

Product 1

HCID 22716425HCID 22716425, compoundYield 73.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Compound 39 (50 mg, 0.112 mmol) was hydrogenated in ethyl acetate (40 mL) at 30 lb./sq. in. using 10% palladium on carbon (15 mg) as catalyst for 16 hours. The solution was passed through a Celite bed and the catalyst was washed with ethyl acetate (10 mL×3). Concentration of the ethyl acetate solution in vacuo gave a crude product. Column chromatography was performed using a 35:65 mixture of hexanes:ethyl acetate as eluting solvent to give two compounds. The compound having the higher Rf material on thin layer chromatography was isolated as compound 41 (34 mg, 73%); IR (KBr) 3446, 2932, 1610, 1509, 1461, 1421, 1254 cm−1; 1H NMR (CDCl3) δ3.90 (3H, s), 4.01 (3H, s), 4.02 (3H, s), 5.08 (2H. s), 6.42 (1H, s), 6.87 (1H, s), 7.12 (1H, s), 7.15 (1H, s), 7.33-7.48 (6H, m), 7.71-7.75 (2H, m); 13C NMR δ56.40, 56.42, 56.48, 73.07, 101.48, 106.59, 106.78, 119.09, 119.96, 126.24, 126.78, 127.29, 128.16, 128.20, 128.45, 128.90, 129.86, 135.56, 138.19, 138.88, 141.70, 150.07, 150.30, 150.92; HRMS (EI) calcd for C26H25NO4 m/z: 415.1784; found: 415.1775.

Workup

  1. customfor 16 hours
  2. washthe catalyst was washed with ethyl acetate (10 mL×3)
  3. customConcentration of the ethyl acetate solution in vacuo gave a crude product
  4. washethyl acetate as eluting solvent
  5. customto give two compounds

Sources & evidence

ORD record
ord-56b4bc8c69ad4ff79cd1ce5c185bc3f1
Source dataset
uspto-grants-2004_05
Patent number
US06740650B2

Reaction notes

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