Hydrogen Peroxide → HCID 58052401, compound

HRID 2190203Notes

Reaction equation

HRID 2190203 reaction equation
OO.C([C@H]1COC(=O)N1[C:16](=[O:50])[C@@H:17]([CH3:49])[CH2:18][CH2:19][CH2:20][N:21]([C:26]1[N:31]=[C:30]2[O:32][C:33]([C:39]3[CH:44]=[CH:43][C:42]([CH3:45])=[CH:41][CH:40]=3)=[C:34]([C:35]([NH:37][CH3:38])=[O:36])[C:29]2=[CH:28][C:27]=1[CH:46]1[CH2:48][CH2:47]1)[S:22]([CH3:25])(=[O:24])=[O:23])C1C=CC=CC=1.[Li+].[OH-].S([O-])([O-])=[O:54].[Na+].[Na+].C(=O)(O)[O-].[Na+]>C1COCC1.O.O.CO.C(Cl)Cl>[CH:46]1([C:27]2[CH:28]=[C:29]3[C:34]([C:35](=[O:36])[NH:37][CH3:38])=[C:33]([C:39]4[CH:40]=[CH:41][C:42]([CH3:45])=[CH:43][CH:44]=4)[O:32][C:30]3=[N:31][C:26]=2[N:21]([CH2:20][CH2:19][CH2:18][C@H:17]([CH3:49])[C:16]([OH:54])=[O:50])[S:22]([CH3:25])(=[O:24])=[O:23])[CH2:47][CH2:48]1

Participants

10

Reactant 5

HCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 24437Sodium SulfiteHCID 516892Sodium BicarbonateHCID 58052524HCID 58052524, compound

Product 1

HCID 58052401HCID 58052401, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

H2O2 (30%) (0.222 mL, 2.170 mmol) was added to a solution of 6-(N—((S)-5-((S)-4-benzyl-2-oxooxazolidin-3-yl)-4-methyl-5-oxopentyl)methylsulfonamido)-5-cyclopropyl-N-methyl-2-p-tolylfuro[2,3-b]pyridine-3-carboxamide (365 mg, 0.543 mmol) in 6.4 mL of 7:3 THF/water at 0° C. Added LiOH (26.0 mg, 1.085 mmol) Stirred at 0° C. for 15 min. Quenched with sodium sulfite (342 mg, 2.71 mmol) in 2 mL water followed by sodium bicarbonate (0.5 M) (5.43 mL, 2.71 mmol) Added DCM and extracted AQ layer Treated AQ layer with 1N HCl and then extracted with EtOAc. Concentrated Chiral HPLC using a 20-250 mm IA column running 40% EtOH in heptane gave 294 mg (0.572 mmol) desired enantiomer at 9.4 min. and 120 mg of undesired enantiomer at 13.3 min. The desired enantiomer was taken up in 2 mL MeOH and salted with 0.5 N KHCO3 and lyophylized.

Workup

  1. extractionextracted AQ layer
  2. additionTreated AQ layer with 1N HCl
  3. extractionextracted with EtOAc
  4. customgave 294 mg (0.572 mmol) desired enantiomer at 9.4 min.

Sources & evidence

ORD record
ord-e31981e125694375973f42d4d321ce04
Source dataset
uspto-grants-2012_12
Patent number
US08324239B2

Reaction notes

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