HCID 68864404, compound → HCID 68863577, compound

HRID 1725981Notes

Reaction equation

HRID 1725981 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[CH:21]=[CH:20][C:19]2[CH2:18][CH2:17][CH:16]=[C:15]([O:22][CH3:23])[C:14]=2[C:13]=1[C:24]([O:26][CH3:27])=[O:25])(=[O:10])=[O:9].[H][H]>C(OCC)(=O)C.[Pd]>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[CH:21]=[CH:20][C:19]2[CH2:18][CH2:17][CH2:16][CH:15]([O:22][CH3:23])[C:14]=2[C:13]=1[C:24]([O:26][CH3:27])=[O:25])(=[O:10])=[O:9]

Participants

5

Reactant 2

HCID 68864404HCID 68864404, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68863577HCID 68863577, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of Example 458B (352 mg, 0.9 mmol) and 10% Pd/C (99.8 mg) in ethyl acetate (18 mL) was hydrogenated under 50 psi of hydrogen for 2.5 days. After filtration and concentration, the desired product was isolated in quantitative yield. MS (DCI/NH3) m/e 411 (M+NH4)+; 1H NMR (300 MHz, DMSO-d6) δ 9.84 (s, 1H), 7.7-7.61 (m, 2H), 7.43 (m, 1H), 7.31 (t, 1H), 7.12 (d, 1H), 7.01 (d, 1H), 4.42 (t, 1H), 3.63 (s, 3H), 3.15 (s, 3H), 2.70-2.61 (m, 2H), 1.86 (m, 1H), 1.77-1.55 (m, 3H).

Workup

  1. filtrationAfter filtration and concentration

Sources & evidence

ORD record
ord-66af27dc03f241e7bbb9095243b0a315
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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