Hydrogen Peroxide → HCID 67271210, compound

HRID 601708Notes

Reaction equation

HRID 601708 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:52]=[C:53]([F:55])[CH:54]=1)[CH2:5][C@H:6]([C:37](N1[C@@H](CC2C=CC=CC=2)COC1=O)=[O:38])[C@@H:7]([CH:9]1[CH2:18][C:17]2[C:12](=[C:13]([O:19][Si:20]([CH:27]([CH3:29])[CH3:28])([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22])[CH:14]=[CH:15][CH:16]=2)[CH2:11][N:10]1[C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[OH:8].[Li+].[OH-:57].OO>C1COCC1.O>[F:55][C:53]1[CH:52]=[C:4]([CH:3]=[C:2]([F:1])[CH:54]=1)[CH2:5][C@@H:6]([C@@H:7]([CH:9]1[CH2:18][C:17]2[C:12](=[C:13]([O:19][Si:20]([CH:27]([CH3:29])[CH3:28])([CH:24]([CH3:25])[CH3:26])[CH:21]([CH3:23])[CH3:22])[CH:14]=[CH:15][CH:16]=2)[CH2:11][N:10]1[C:30]([O:32][C:33]([CH3:34])([CH3:36])[CH3:35])=[O:31])[OH:8])[C:37]([OH:57])=[O:38]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 67271352HCID 67271352, compound

Product 1

HCID 67271210HCID 67271210, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 3-((1S,2S)-2-(3,5-difluorobenzyl)-3-((S)-4-benzyl-2-oxooxazolidin-3-yl)-1-hydroxy-3-oxopropyl)-8-(triisopropylsilyloxy)-3,4-dihydroisoquinoline-2(1H)-carboxylate (Step F (9), 2.0 g, 2.57 mmol) in THF (50 mL) was added a solution of LiOH (123 mg, 5.13 mmol) in H2O (8 mL), then 30% H2O2 (3.0 g, 25.7 mmol) was added at −5° C. This reaction mixture was stirred from −5° C. to 0° C. over 1 h and stirred at rt for 3 h. Solvent was removed and ethyl acetate (500 mL) was added. The mixture was 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)− 618.22.

Workup

  1. stirringstirred at rt for 3 h
  2. customSolvent was removed
  3. additionethyl acetate (500 mL) was added
  4. washThe mixture was washed with 1N HCl, and H2O
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3ea776c2c8744b02bee10f241f47df73
Source dataset
uspto-grants-2011_03
Patent number
US07902218B2

Reaction notes

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