Hydrogen Peroxide → (25,35)-2-azido-3-(1-(tert-butoxycarbonyl)-1H-indol-3-yl)butanoic acid

HRID 625893Notes

Reaction equation

HRID 625893 reaction equation
[N:1]([C@H:4]([C:23](=[O:36])N1[C@H](C2C=CC=CC=2)COC1=O)[C@H:5]([C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:8]=1)[CH3:6])=[N+:2]=[N-:3].OO.[OH-:39].[Li+]>O.C1COCC1>[N:1]([C@@H:4]([C@H:5]([C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]([C:16]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:17])[CH:8]=1)[CH3:6])[C:23]([OH:36])=[O:39])=[N+:2]=[N-:3]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 11213980tert-butyl 3-((2S,3S)-3-azido-4-oxo-4-((R)-2-oxo-4-phenyloxazolidin-3-yl)butan-2-yl)-1H-indole-1-carboxylate

Product 1

HCID 11244851(25,35)-2-azido-3-(1-(tert-butoxycarbonyl)-1H-indol-3-yl)butanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of tert-butyl 3-((2S,3S)-3-azido-4-oxo-4-((R)-2-oxo-4-phenyloxazolidin-3-yl)butan-2-yl)-1H-indole-1-carboxylate (3.38 g, 6.90 mmol) in Water (29 mL) and THF (86 mL) at 0° C. was added hydrogen peroxide (4.67 ml, 45.7 mmol), then lithium hydroxide (0.331 g, 13.81 mmol). The reaction was stirred for 2 h. The reaction was quenched with Na2SO3 (7 g) in 40 mL water. The reaction was stirred for 30 min at rt. The solvent was removed under vacuum and then the reaction was diluted with EtOAc and water. The pH was adjusted to 2. The organic phase was collected, washed with brine, dried over sodium sulfate and concentrated under vacuum to give a residue which was triturated in Et2O to give a solid which was collected by filtration and dried to give (2S,3S)-2-azido-3-(1-(tert-butoxycarbonyl)-1H-indol-3-yl)butanoic acid, 2.38 g (100%). ESI-MS(−) m/z 343.3 (M−H). 1H NMR (500 MHz, chloroform-d) d 8.15 (d, J=5.5 Hz, 1H), 7.60 (d, J=7.7 Hz, 1H), 7.58-7.55 (m, 1H), 7.33 (td, J=7.7, 1.1 Hz, 1H), 7.27-7.23 (m, 1H), 4.29 (d, J=6.5 Hz, 1H), 3.68 (quin, J=6.9 Hz, 1H), 1.70 (s, 9H), 1.51 (d, J=7.1 Hz, 3H).

Workup

  1. customThe reaction was quenched with Na2SO3 (7 g) in 40 mL water
  2. stirringThe reaction was stirred for 30 min at rt
  3. customThe solvent was removed under vacuum
  4. additionthe reaction was diluted with EtOAc and water
  5. customThe organic phase was collected
  6. washwashed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under vacuum
  9. customto give a residue which
  10. customwas triturated in Et2O
  11. customto give a solid which
  12. filtrationwas collected by filtration
  13. customdried

Sources & evidence

ORD record
ord-2a8f7f57aca1466bbb1d486ff64b6c50
Source dataset
uspto-grants-2016_04
Patent number
US09308236B2

Reaction notes

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