Hydrochloric Acid → HCID 12084906, compound

HRID 1795487Notes

Reaction equation

HRID 1795487 reaction equation
C(OC(N[CH:12]1[NH:16][C@@H:15]([CH3:17])[C:14]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=2[F:26])([OH:18])[O:13]1)=O)C1C=CC=CC=1.[OH2:27].Cl>O1CCCC1.C1(C)C=CC=CC=1>[CH2:14]([O:27][C:12]([NH:16][C@@H:15]([CH3:17])[C:14]([C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=1[F:26])=[O:18])=[O:13])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 69599571HCID 69599571, compound

Product 1

HCID 12084906HCID 12084906, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

In tetrahydrofuran (70 mL) was dissolved (4S)-2-(benzyloxycarbonyl)amino-5-(2,4-difluorophenyl)-4-methyl-5-hydroxyoxazolidine (14.0 g) prepared in Example 12, and water (50 mL) and conc. hydrochloric acid (20 mL) were added. The mixture was stirred at room temperature for 24 hours. The reaction mixture was diluted with toluene, the aqueous layer was discarded, and the organic layer was washed with water three times. The organic layer was dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by silica column chromatography (eluent: hexane/ethyl acetate=3/1) to give the title compound (11.7 g) as a pale yellow syrup in a yield of 92%.

Workup

  1. additionwere added
  2. washthe organic layer was washed with water three times
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica column chromatography (eluent: hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-812960d900674bc9a6d5ebf2f313e114
Source dataset
uspto-grants-2006_04
Patent number
US07026515B2

Reaction notes

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