Hydrogen Peroxide → HCID 29947824, compound

HRID 82387Notes

Reaction equation

HRID 82387 reaction equation
OO.C([C@@H]1COC(=O)N1[C:16](=[O:34])[C@@H:17]([C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=1)[CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])C1C=CC=CC=1.C[O:36]C1C=C(OC)C=CC=1C=O.[O-]S([O-])=O.[Na+].[Na+]>C1COCC1.O>[C:22]([O:21][C:20]([NH:19][CH2:18][C@H:17]([C:27]1[CH:28]=[CH:29][C:30]([Cl:33])=[CH:31][CH:32]=1)[C:16]([OH:34])=[O:36])=[O:26])([CH3:23])([CH3:24])[CH3:25]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 24437Sodium SulfiteHCID 691752,4-DimethoxybenzaldehydeHCID 70677261tert-butyl (S)-3-((R)-4-benzyl-2-oxooxazolidin-3-yl)-2-(4-chlorophenyl)-3-oxopropylcarbamate

Product 1

HCID 29947824HCID 29947824, compoundYield 94.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

35% H2O2 (0.240 mL, 2.91 mmol) was added to a solution of LiO—H2O (0.0978 g, 2.33 mmol) in 2:1 THF:H2O (33 mL). The reaction mixture was stirred at room temperature for 35 minutes and then cooled to 0° C. A solution containing a mixture of tert-butyl (S)-3-((R)-4-benzyl-2-oxooxazolidin-3-yl)-2-(4-chlorophenyl)-3-oxopropylcarbamate (0.535 g, 1.17 mmol) and 2,4-dimethoxybenzaldehyde (0.194 g, 1.17 mmol) in THF (7 mL) was added dropwise by addition funnel. The reaction mixture was placed in an ice bath to slowly warm the reaction mixture and it was stirred overnight. The reaction mixture was then cooled to 0° C., and 1M Na2SO3 (7 mL) was added to the mixture. The mixture was stirred for 5 minutes and then warmed to room temperature while being stirred for 20 minutes. The reaction mixture was then transferred to a separatory funnel and washed with ether (3×). The aqueous layer was acidified with KHSO4(s), and the mixture was extracted with DCM (2×). The combined extracts were dried (Na2SO4), filtered, and concentrated to give (S)-3-(tert-butoxycarbonylamino)-2-(4-chlorophenyl)propanoic acid (0.329 g, 94.2% yield) as a white residue. LC/MS (APCI+) m/z 200 [M−BOC+H]+.

Workup

  1. temperaturecooled to 0° C
  2. additionA solution containing
  3. additionwas added dropwise by addition funnel
  4. customThe reaction mixture was placed in an ice bath
  5. temperatureto slowly warm the reaction mixture and it
  6. stirringwas stirred overnight
  7. temperatureThe reaction mixture was then cooled to 0° C.
  8. stirringThe mixture was stirred for 5 minutes
  9. temperaturewarmed to room temperature
  10. stirringwhile being stirred for 20 minutes
  11. customThe reaction mixture was then transferred to a separatory funnel
  12. washwashed with ether (3×)
  13. extractionthe mixture was extracted with DCM (2×)
  14. dry with materialThe combined extracts were dried (Na2SO4)
  15. filtrationfiltered
  16. concentrationconcentrated

Sources & evidence

ORD record
ord-d5ad9419dd514c3db2b3f6540b0cce03
Source dataset
uspto-grants-2014_09
Patent number
US08846681B2

Reaction notes

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