2-Iodoxybenzoic acid → (2R)-1-benzyl-N-(4-(ethoxyamino)-3,4-dioxo-1-phenylbutan-2-yl)-5-oxopyrrolidine-2-carboxamide

HRID 1474149Notes

Reaction equation

HRID 1474149 reaction equation
I(C1C=CC=CC=1C(O)=O)(=O)=O.[CH2:13]([N:20]1[C:24](=[O:25])[CH2:23][CH2:22][C@@H:21]1[C:26]([NH:28][CH:29]([CH:37]([OH:44])[C:38]([NH:40][O:41][CH2:42][CH3:43])=[O:39])[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:27])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C([O-])(O)=O.[Na+]>CS(C)=O.O.ClCCl>[CH2:13]([N:20]1[C:24](=[O:25])[CH2:23][CH2:22][C@@H:21]1[C:26]([NH:28][CH:29]([C:37](=[O:44])[C:38]([NH:40][O:41][CH2:42][CH3:43])=[O:39])[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:27])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

7

Reactant 3

HCID 1087942-Iodoxybenzoic acid2×HCID 516892Sodium BicarbonateHCID 86652462(2R)-1-benzyl-N-(4-(ethoxyamino)-3-hydroxy-4-oxo-1-phenylbutan-2-yl)-5-oxopyrrolidine-2-carboxamide

Product 1

HCID 53257548(2R)-1-benzyl-N-(4-(ethoxyamino)-3,4-dioxo-1-phenylbutan-2-yl)-5-oxopyrrolidine-2-carboxamideYield 3.02%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

IBX (2-iodoxybenzoic acid 432 mg, 0.694 mmol) was added to a solution of (2R)-1-benzyl-N-(4-(ethoxyamino)-3-hydroxy-4-oxo-1-phenylbutan-2-yl)-5-oxopyrrolidine-2-carboxamide (218 mg, 0.496 mmol) in DMSO (2 ml). After stirring for 2 h at room temperature more IBX (123 mg, 0.198 mmol) was added and the stirring was continued overnight. Saturated aqueous NaHCO3 solution was added and the reaction mixture was diluted with water and dichloromethane. The precipitate formed was filtered off, the organic layer was separated and the aqueous layer extracted with dichloromethane. The combined organic layers were washed with water and dried (MgSO4). The solvent was removed in vacuo, the resulting residue was redissolved in a small amount of dichloromethane and diethylether was added. The white precipitate formed was filtered, washed with diethylether and dried in vacuo. The crude product was dissolved in dichloromethane and treated with three drops of aqueous HCl (4M in dioxane). Removal of the solvent provided the title compound (8.2 mg, 0.015 mmol, 3.02% yield). ESI-MS [M+H]+=438.2

Workup

  1. additionwas added
  2. customThe precipitate formed
  3. filtrationwas filtered off
  4. customthe organic layer was separated
  5. extractionthe aqueous layer extracted with dichloromethane
  6. washThe combined organic layers were washed with water
  7. dry with materialdried (MgSO4)
  8. customThe solvent was removed in vacuo
  9. dissolutionthe resulting residue was redissolved in a small amount of dichloromethane and diethylether
  10. additionwas added
  11. customThe white precipitate formed
  12. filtrationwas filtered
  13. washwashed with diethylether
  14. customdried in vacuo
  15. dissolutionThe crude product was dissolved in dichloromethane
  16. additiontreated with three drops of aqueous HCl (4M in dioxane)
  17. customRemoval of the solvent

Sources & evidence

ORD record
ord-d20bcb500b2746b5b13e86056b0f1d0e
Source dataset
uspto-grants-2015_04
Patent number
US09018206B2

Reaction notes

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