Hydrogen Peroxide → HCID 19705451, compound

HRID 727576Notes

Reaction equation

HRID 727576 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:35]=[CH:36][C:37]=1[F:38])[C:5]([NH:7][CH2:8][CH2:9][CH:10]([C:18]1([C:32](C)=[CH2:33])[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]1=[O:31])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:6].[OH-].[Na+].OO.C1C[O:46][CH2:45]C1>>[F:1][C:2]1[CH:3]=[C:4]([CH:35]=[CH:36][C:37]=1[F:38])[C:5]([NH:7][CH2:8][CH2:9][CH:10]([C:18]1([CH2:32][CH2:33][CH2:45][OH:46])[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:19]1=[O:31])[C:11]([O:13][C:14]([CH3:15])([CH3:17])[CH3:16])=[O:12])=[O:6]

Participants

5

Reactant 4

HCID 784Hydrogen PeroxideHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 19705462HCID 19705462, compound

Product 1

HCID 19705451HCID 19705451, compound

Procedure

A cold (0° C.) solution of tert-butyl α-[2-[(3,4-difluorobenzoyl)amino]ethyl]-2-oxo-1-(2-phenylethyl)-3-(propen-2-yl)-3-pyrrolidineacetate (1.62 g, 3.07 mmol) in dry THF (10 mL) is treated with monochloroborane methylsulfide complex (640 μL, 6.14 mmol). The ice bath is removed, and after 4.5 h, 3N NaOH (7.4 mL, 22.1 mmol) is added dropwise, followed by 30% H2O2 (2.5 mL). The solution is stirred for 1 hour at room temperature and then for 1 hour at 50° C. After cooling to room temperature and dilution with saturated NH4Cl (5 mL) and H2O (15 mL), the product is extracted into EtOAc (3×50 mL). The extracts are combined, dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure to give 1.6 g of a yellow gel. The material is purified by silica gel chromatography (75 g SG; 75% EtOAc/hexane) to provide 713 mg (43%) of the title compound as a white, amorphous solid:

Workup

  1. customThe ice bath is removed
  2. waitfor 1 hour at 50° C
  3. temperatureAfter cooling to room temperature
  4. extractiondilution with saturated NH4Cl (5 mL) and H2O (15 mL), the product is extracted into EtOAc (3×50 mL)
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6867efad7f764f5eb48967360a8cf690
Source dataset
uspto-grants-1998_01
Patent number
US05712300

Reaction notes

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