HCID 68840252, compound → HCID 57777289, compound

HRID 660539Notes

Reaction equation

HRID 660539 reaction equation
C([O:8][C:9]1[CH:14]=[C:13]([CH2:15][C@@H:16]2[CH2:20][CH2:19][C:18](=[O:21])[NH:17]2)[CH:12]=[CH:11][C:10]=1[N:22]1[S:26](=[O:28])(=[O:27])[NH:25][C:24](=[O:29])[CH2:23]1)C1C=CC=CC=1>CCO.O.[Pd]>[OH:8][C:9]1[CH:14]=[C:13]([CH2:15][C@@H:16]2[CH2:20][CH2:19][C:18](=[O:21])[NH:17]2)[CH:12]=[CH:11][C:10]=1[N:22]1[S:26](=[O:28])(=[O:27])[NH:25][C:24](=[O:29])[CH2:23]1

Participants

4

Reactant 1

HCID 68840252HCID 68840252, compound

Product 1

HCID 57777289HCID 57777289, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 19096565Water ethanolSolvent

Procedure

To a solution of 5-[2-benzyloxy-4-((S)-5-oxopyrrolidin-2-ylmethyl)-phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one (0.017 g, 0.041 mmol) in EtOH/H2O (1:1, 10 mL) is added 10% Pd/C (0.010 g). The mixture is stirred under an atmosphere of H2 for 2 h at RT. The catalyst is filtered through Celite and is washed with EtOH. The solvent is evaporated off to the title compound. 1H NMR (DMSO-d6) δ 7.16 (d, J=8 Hz, 1H), 6.53 is, 1H), 6.36 (d, J=5.81 Hz, 1H), 4.08 (s, 2H), 2.42 (m, 2H), 2.07 (t, J=6.57 Hz, 2H), 1.51 (m, 3H); HPLC retention time=0.55 min (method A). (M−H)−=326.

Workup

  1. filtrationThe catalyst is filtered through Celite
  2. washis washed with EtOH
  3. customThe solvent is evaporated off to the title compound

Sources & evidence

ORD record
ord-6b12aa99652b41789fae9a9f871f9926
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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