{(E)-3-[3-Benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-1,1-dimethylallyl}-carbamic Acid Tert-butyl Ester → {3-[3-Hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-1,1-dimethylpropyl}-carbamic Acid Tert-butyl Ester

HRID 660526Notes

Reaction equation

HRID 660526 reaction equation
[C:1]([O:5][C:6](=[O:35])[NH:7][C:8]([CH3:34])([CH3:33])/[CH:9]=[CH:10]/[C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:21][C:20](=[O:22])[NH:19][S:18]2(=[O:24])=[O:23])=[C:13]([O:25]CC2C=CC=CC=2)[CH:12]=1)([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6](=[O:35])[NH:7][C:8]([CH3:34])([CH3:33])[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:21][C:20](=[O:22])[NH:19][S:18]2(=[O:24])=[O:23])=[C:13]([OH:25])[CH:12]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 68843602{(E)-3-[3-Benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-1,1-dimethylallyl}-carbamic Acid Tert-butyl Ester

Product 1

HCID 42629543{3-[3-Hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-1,1-dimethylpropyl}-carbamic Acid Tert-butyl Ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of {(E)-3-[3-benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-1,1-dimethylallyl}-carbamic acid tert-butyl ester (105 mg, 0.2 mmol) in ethanol (5 mL) is hydrogenated over 10% Pd/C at 1 atm for 18 h. The catalyst is removed by filtration through Celite and the solvent is removed under reduced pressure to give the title compound. It is converted to a potassium salt by addition of 1 equivalent of KHCO3. 1H NMR (400 MHz, MeOD) δ ppm 1.17 (s, 6 H) 1.34 (s, 9 H) 1.77-1.87 (m, 2 H) 2.35-2.44 (m, 2 H) 4.20 (s, 2 H) 6.59 (dd, J=8.08, 1.77 Hz, 1 H) 6.65 (d, J=1.77 Hz, 1 H) 7.20 (d, J=8.08 Hz, 1 H) LCMS (method A) retention time=1.32 min, (M−H)−=142

Workup

  1. customThe catalyst is removed by filtration through Celite
  2. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-4995ef207e484e4996ad799f1c42b018
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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