Hydrogen Peroxide → HCID 57881052, compound

HRID 601702Notes

Reaction equation

HRID 601702 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:41]=[C:42]([F:44])[CH:43]=1)[CH2:5][C@H:6]([C:26](N1[C@@H](CC2C=CC=CC=2)COC1=O)=[O:27])[C@@H:7]([C@H:9]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][N:10]1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[OH:8].[Li+].[OH-].OO.C(OCC)(=[O:51])C>C1COCC1.O>[F:44][C:42]1[CH:41]=[C:4]([CH:3]=[C:2]([F:1])[CH:43]=1)[CH2:5][C@@H:6]([C@@H:7]([C@H:9]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][N:10]1[C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])[OH:8])[C:26]([OH:51])=[O:27]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 67271761(R)-tert-butyl 3-((1S,2S)-2-(3,5-difluorobenzyl)-3-((S)-4-benzyl-2-oxooxazolidin-3-yl)-1-hydroxy-3-oxopropyl)-3,4-dihydro-isoquinoline-2(1H)-carboxylate

Product 1

HCID 57881052HCID 57881052, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-tert-butyl 3-((1S,2S)-2-(3,5-difluorobenzyl)-3-((S)-4-benzyl-2-oxooxazolidin-3-yl)-1-hydroxy-3-oxopropyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (Step A (4), 13.0 g, 21.5 mmol) in THF (500 mL) was added a solution of LiOH (1.03 g, 43 mmol) in H2O (100 mL), then 30% H2O2 (24.4 g) was added at 0° C. This reaction mixture was warmed up to rt over 1 h and stirred at rt for 4 h. Ethyl acetate (1000 mL) was added and washed with 1N HCl, and H2O, dried (Na2SO4), and concentrated in vacuo to give the crude product which was ready for next step without purification. MS (ESI) (M−H)− 446.07.

Workup

  1. washwashed with 1N HCl, and H2O
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dcd4b813013440a5af3f70595aa9ebe3
Source dataset
uspto-grants-2011_03
Patent number
US07902218B2

Reaction notes

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