Hydrochloric Acid → HCID 9822766, compound

HRID 1634531Notes

Reaction equation

HRID 1634531 reaction equation
[CH2:1]([CH:3]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([C:28](=[O:41])[NH:29][CH2:30][C:31]2[CH:36]=[CH:35][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:33][CH:32]=2)[CH:21]=1)[C:4](N1[C@@H](CC2C=CC=CC=2)COC1=O)=[O:5])[CH3:2].[OH:42]O.O.[OH-].[Li+].Cl>O.O1CCCC1>[CH2:1]([CH:3]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([C:28](=[O:41])[NH:29][CH2:30][C:31]2[CH:32]=[CH:33][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:35][CH:36]=2)[CH:21]=1)[C:4]([OH:5])=[O:42])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 168937Lithium hydroxide, monohydrateHCID 69758312HCID 69758312, compound

Product 1

HCID 9822766HCID 9822766, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 8028TetrahydrofuranSolvent

Procedure

(4S)-3-[2-ethyl-3-[4-methoxy-3-[N-[[4-(trifluoromethyl)phenyl]methyl]carbamoyl]phenyl]propionyl]-4-benzyl-2-oxazolidinone (860 mg, 1.51 mmol) was mixed with 8 ml of mixed solution of tetrahydrofuran with water (4:1 v/v), which was cooled with ice under an atmosphere of argon. Under stirring, 611 ml of 30% aqueous hydrogen peroxide was added over 2 minutes, further 101 mg of lithium hydroxide monohydrate dissolved in 2.7 ml of water was added thereto over 2 minutes. After the mixture was stirred for 1 hour under cooling with ice, sodium sulfite 7-hydrate dissolved in 4 ml of water was added, and the mixture was stirred for 5 minutes at 0° C. The reaction mixture was poured into 5% aqueous solution of hydrochloric acid, which was extracted with ethyl acetate. The extract was washed with brine, then dried over anhydrous magnesium sulfate and concentrated. The residue was crystallized by adding ethyl acetate and n-hexane to obtain 125 mg (20%) of the title compound as colorless prisms.

Workup

  1. temperaturewas cooled with ice under an atmosphere of argon
  2. additionwas added
  3. stirringAfter the mixture was stirred for 1 hour
  4. additionwas added
  5. stirringthe mixture was stirred for 5 minutes at 0° C
  6. extractionwas extracted with ethyl acetate
  7. washThe extract was washed with brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated
  10. customThe residue was crystallized
  11. additionby adding ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-302daeaae7024fd0a2175902afbe7917
Source dataset
uspto-grants-2003_01
Patent number
US06506797B1

Reaction notes

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