Ammonium formate → N-Hydroxy-3-(2-methylpropyl)-2,5-dioxo-1-(2-phenylethyl)-3-pyrrolidineacetamide

HRID 727557Notes

Reaction equation

HRID 727557 reaction equation
C([O:8][NH:9][C:10](=[O:31])[CH2:11][C:12]1([CH2:27][CH:28]([CH3:30])[CH3:29])[CH2:16][C:15](=[O:17])[N:14]([CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:13]1=[O:26])C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].CCO>[OH:8][NH:9][C:10](=[O:31])[CH2:11][C:12]1([CH2:27][CH:28]([CH3:29])[CH3:30])[CH2:16][C:15](=[O:17])[N:14]([CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:13]1=[O:26]

Participants

5

Reactant 2

HCID 2723923Ammonium formate2×HCID 53945587N-Benzyloxy-3-(2-methylpropyl)-2,5-dioxo-1-(2-phenylethyl)-3-pyrrolidineacetamide

Product 1

HCID 17894887N-Hydroxy-3-(2-methylpropyl)-2,5-dioxo-1-(2-phenylethyl)-3-pyrrolidineacetamideYield 31%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of N-benzyloxy-3-(2-methylpropyl)-2,5-dioxo-1-(2-phenylethyl)-3-pyrrolidineacetamide (80 mg, 0.19 mmol), Pd/C (10%, 5 mg), ammonium formate (59 mg, 0.95 mmol) and EtOH (2.5 mL) is stirred at room temperature. After 2 hours, a second portion of ammonium formate (35 mg, 0.56 mmol) is added and the mixture is allowed to stir overnight at room temperature. The mixture is filtered, and the filter cake washed with MeOH (3×15 mL) and CHCl3 (3×15 mL). The filtrate is concentrated, reconstituted in 100 mL of 5% MeOH/CHCl3, dried (MgSO4), filtered and concentrated to an oil. Crystallization from CH2Cl2 /Et2 O/hexane gives 19 mg (31%) of the title compound as a white solid (mp 136°-137° C.).

Workup

  1. stirringto stir overnight at room temperature
  2. filtrationThe mixture is filtered
  3. washthe filter cake washed with MeOH (3×15 mL) and CHCl3 (3×15 mL)
  4. concentrationThe filtrate is concentrated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated to an oil
  8. customCrystallization from CH2Cl2 /Et2 O/hexane

Sources & evidence

ORD record
ord-aa4ec1c106c94b409e4f80ccbdc85d05
Source dataset
uspto-grants-1998_01
Patent number
US05712300

Reaction notes

Loading…