HCID 69001892, compound → HCID 57777439, compound

HRID 660701Notes

Reaction equation

HRID 660701 reaction equation
[K].C([O:9][C:10]1[CH:15]=[C:14]([CH2:16][CH:17]([CH3:22])[C:18](=[O:21])[CH2:19][CH3:20])[CH:13]=[CH:12][C:11]=1[N:23]1[S:27](=[O:29])(=[O:28])[NH:26][C:25](=[O:30])[CH2:24]1)C1C=CC=CC=1>CCO.O.[Pd]>[OH:9][C:10]1[CH:15]=[C:14]([CH2:16][CH:17]([CH3:22])[C:18](=[O:21])[CH2:19][CH3:20])[CH:13]=[CH:12][C:11]=1[N:23]1[S:27](=[O:29])(=[O:28])[NH:26][C:25](=[O:30])[CH2:24]1

Participants

4

Reactant 1

HCID 69001892HCID 69001892, compound

Product 1

HCID 57777439HCID 57777439, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 19096565Water ethanolSolvent

Procedure

To a solution of 5-[2-benzyloxy-4-(2-methyl-3-oxo-pentyl)-phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one potassium salt in 5 mL of EtOH/water (1:1)) is added 20 mg of Degussa Pd/C and the resulting mixture is hydrogenated at 1 atm for 30 min. The catalyst is filtered through Celite and the solvent is removed under reduced pressure. The residue is purified by preparative HPLC to give the title compound: 1H NMR (Acetonitrile-d3) δ 7.30 (d, J=8.0 Hz, 1H), 6.79 (m, 1H), 6.75 (dd, J=8.0, 2.0 Hz, 1H), 4.38 (s, 2H), 2.83 (m, 2H), 2.46 (m, 2H), 2.29 (m, 1H), 1.01 (m, 3H), 0.9 (t, J=7.33 Hz, 3H). (M−1)−=325. HPLC retention time=0.92 min (Method A).

Workup

  1. filtrationThe catalyst is filtered through Celite
  2. customthe solvent is removed under reduced pressure
  3. customThe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-362a28ac795e47d5858dbd20d66842e1
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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