2-Iodoxybenzoic acid → HCID 86647370, compound

HRID 2061684Notes

Reaction equation

HRID 2061684 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:43])[C:38]([NH:40][O:41][CH3:42])=[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.C(Cl)Cl.C(OCC)C>[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:43])[C:38]([NH:40][O:41][CH3:42])=[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

8

Reactant 3

HCID 1087942-Iodoxybenzoic acid2×HCID 516892Sodium BicarbonateHCID 86647371HCID 86647371, compound

Product 1

HCID 86647370HCID 86647370, compound

Reagents, catalysts & solvents 4

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

IBX (293 mg, 0.472 mmol) was added to a solution of (2R)-1-benzyl-N-(3-hydroxy-4-(methoxyamino)-4-oxo-1-phenylbutan-2-yl)-5-oxopyrrolidine-2-carboxamide (143 mg, 0.337 mmol) in DMSO (5 mL). After stirring for 2 h more IBX (105 mg, 0.169 mmol) was added and the stirring continued overnight. The saturated aqueous NaHCO3 solution was added and the reaction mixture was diluted with water and DCM. The organic layer was separated and the aqueous layer was extracted with DCM. The combined organic layers were washed with water and dried (MgSO4). The crude product obtained was dissolved in a minimal amount of DCM and diethylether was added. The precipitate formed was isolated and dried in vacuo. The title compound was obtained as a colourless solid (12 mg, 8%)

Workup

  1. additionwas added
  2. customthe stirring continued overnight
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with DCM
  5. washThe combined organic layers were washed with water
  6. dry with materialdried (MgSO4)
  7. customThe crude product obtained
  8. additionwas added
  9. customThe precipitate formed
  10. customwas isolated
  11. customdried in vacuo

Sources & evidence

ORD record
ord-27e4edc1baab4a2fb36b7362cba2092d
Source dataset
uspto-grants-2012_10
Patent number
US08283363B2

Reaction notes

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