2-Iodoxybenzoic acid → HCID 86647370, compound

HRID 882848Notes

Reaction equation

HRID 882848 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 stiffing 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. customthe stirring continued overnight
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with DCM
  4. washThe combined organic layers were washed with water
  5. dry with materialdried (MgSO4)
  6. customThe crude product obtained
  7. additionwas added
  8. customThe precipitate formed
  9. customwas isolated
  10. customdried in vacuo

Sources & evidence

ORD record
ord-71923a5df56b4d36884389f96a92f22e
Source dataset
uspto-grants-2012_08
Patent number
US08236798B2

Reaction notes

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