2-Iodoxybenzoic acid → HCID 86647370, compound

HRID 1474141Notes

Reaction equation

HRID 1474141 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-5c6f6bd63f874f21b9d8adf8cada0f2f
Source dataset
uspto-grants-2015_04
Patent number
US09018206B2

Reaction notes

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