HCID 68862448, compound → HCID 68863786, compound

HRID 1726019Notes

Reaction equation

HRID 1726019 reaction equation
[CH2:1]([N:3]([CH2:33][CH3:34])[CH2:4][CH2:5][CH2:6]/[CH:7]=[CH:8]\[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[S:15]([NH:18][C:19]1[CH:28]=[CH:27][C:26]2[CH2:25][CH2:24][CH2:23][CH2:22][C:21]=2[C:20]=1[C:29]([O:31][CH3:32])=[O:30])(=[O:17])=[O:16])[CH3:2]>CO.[Pd]>[CH2:33]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[S:15]([NH:18][C:19]1[CH:28]=[CH:27][C:26]2[CH2:25][CH2:24][CH2:23][CH2:22][C:21]=2[C:20]=1[C:29]([O:31][CH3:32])=[O:30])(=[O:16])=[O:17])[CH3:34]

Participants

4

Reactant 1

HCID 68862448HCID 68862448, compound

Product 1

HCID 68863786HCID 68863786, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A 1:1.2 mixture of Example 595C and Example 596A (408 mg, 0.84 mmol) was hydrogenated over 120 mg of 10% Pd/C in 16 mL of methanol for 1 hour. The reaction mixture was filtered through diatomaceous earth (Celite®), and concentrated to provide 332 mg (81%) of the title compound. 1H NMR (400 MHz, CDCl3) δ 1.16 (t, J=7.14 Hz, 6H) 1.42 (m, 2H) 1.67 (m, 8H) 2.62 (m, 2H) 2.72 (m, 8H) 2.88 (m, 2H) 3.75 (s, 3H) 7.03 (d, J=8.51 Hz, 1H) 7.18 (d, J=8.37 Hz, 1H) 7.22 (m, 1H) 7.29 (dd, J=7.75, 1.17 Hz, 1H) 7.44 (td, J=7.48, 1.37 Hz, 1H) 7.84 (dd, J=7.96, 1.37 Hz, 1H).

Workup

  1. filtrationThe reaction mixture was filtered through diatomaceous earth (Celite®)
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-9f5806d9ef084c79a805d2b0f60b752c
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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