7-[3-Benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-benzyl]-azepan-2-one potassium salt → 7-[3-Hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-benzyl]-azepan-2-one

HRID 660555Notes

Reaction equation

HRID 660555 reaction equation
[K].C([O:9][C:10]1[CH:11]=[C:12]([CH:22]=[CH:23][C:24]=1[N:25]1[CH2:29][C:28](=[O:30])[NH:27][S:26]1(=[O:32])=[O:31])[CH2:13][CH:14]1[NH:20][C:19](=[O:21])[CH2:18][CH2:17][CH2:16][CH2:15]1)C1C=CC=CC=1>CCO.O.[Pd]>[OH:9][C:10]1[CH:11]=[C:12]([CH:22]=[CH:23][C:24]=1[N:25]1[CH2:29][C:28](=[O:30])[NH:27][S:26]1(=[O:32])=[O:31])[CH2:13][CH:14]1[NH:20][C:19](=[O:21])[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

4

Reactant 1

HCID 689945027-[3-Benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-benzyl]-azepan-2-one potassium salt

Product 1

HCID 426296607-[3-Hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-benzyl]-azepan-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 19096565Water ethanolSolvent

Procedure

A solution of 7-[3-benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-benzyl]-azepan-2-one potassium salt in 6 mL of EtOH/water (1:1) is hydrogenated over 10% Pd/C at 1 atm for 2 h. The catalyst is filtered and the solvent is removed under reduced pressure. The residue is purified by reverse phase HPLC followed by lyophilization to give the title compound as a solid: 1H NMR (DMSO-d6): δ 7.85-7.83 (d, J=8.09 Hz, 1H), 7.42-7.41 (d, J=2.02 Hz, 1H), 7.34-7.32 (dd, J=1.77 Hz, 8.09 Hz, 1 H), 6.49-6.50 (d, J=3.53 Hz, 1H), 4.94 (s, 2H), 4.21-4.13 (m, 2H), 3.33-3.20 (m, 3H), 2.98-2.91 (m, 1H), 2.72-2.67 (m, 1H), 2.40-2.21 (m, 3H), 2.08-1.75 (m, 3H). (M−1)−=352.

Workup

  1. filtrationThe catalyst is filtered
  2. customthe solvent is removed under reduced pressure
  3. customThe residue is purified by reverse phase HPLC

Sources & evidence

ORD record
ord-166623d4dd9b444383c9dd83c1770134
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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