HCID 68838974, compound → HCID 57777379, compound

HRID 660597Notes

Reaction equation

HRID 660597 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH2:23][CH2:24][C:25]([N:27]([CH:29]([CH3:31])[CH3:30])[CH3:28])=[O:26])[CH:12]=[CH:13][C:14]=1[N:15]1[CH2:19][C:18](=[O:20])[NH:17][S:16]1(=[O:22])=[O:21])C1C=CC=CC=1>CCOC(C)=O.[Pd]>[OH:8][C:9]1[CH:10]=[C:11]([CH2:23][CH2:24][C:25]([N:27]([CH:29]([CH3:31])[CH3:30])[CH3:28])=[O:26])[CH:12]=[CH:13][C:14]=1[N:15]1[CH2:19][C:18](=[O:20])[NH:17][S:16]1(=[O:22])=[O:21]

Participants

4

Reactant 1

HCID 68838974HCID 68838974, compound

Product 1

HCID 57777379HCID 57777379, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-[3-benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-N-isopropyl-N-methylpropionamide (0.06 g) and 10% Pd/C (0.03 g) in EtOAc (25 mL) is hydrogenated at 1 atm for 18 h. The catalyst is filtered through Celite and the solvent is removed under reduced pressure. The residual gum is purified by preparative HPLC to afford the title compound as a grey solid: 1H NMR (DMSO-d6□7.21 (d, J=8.08 Hz, 1H), 6.73 (s, 1H), 6.66 (d, J=8.08 Hz, 1H), 4.71-4.64 (m, 0.65H), 4.23 (s, 2H), 4.10-4.02 (m, 0.35H), 2.72 (s, 2H), 2.73-2.54 (m, 4H), 2.64 (s, 1H), 1.07 (d, J=6.57 Hz, 2.5H), 0.99 (d, J=6.57 Hz, 3.5H); (M−1)−=354.

Workup

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

Sources & evidence

ORD record
ord-1226869a1db5472c94a13fdc64e79f18
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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