Hydrochloric Acid → HCID 12084904, compound

HRID 1795486Notes

Reaction equation

HRID 1795486 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[C@@H:15]([CH3:16])[C:14]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)(O)[O:13]C1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.Cl>O1CCCC1.C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]([NH:11][C@@H:15]([CH3:16])[C:14]([C:18]1[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=1)=[O:13])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 12084903HCID 12084903, compound

Product 1

HCID 12084904HCID 12084904, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

In tetrahydrofuran (4 mL) was dissolved (4S)-N-benzyloxycarbonyl-5-(4-methoxyphenyl)-4-methyl-5-hydroxyoxazolidine (1.72 g) prepared in Example 10 and then water (5 mL) and conc. hydrochloric acid (2 mL) were added. The mixture was stirred at room temperature for 24 hours. The reaction was diluted with toluene, the aqueous layer was discarded, and then the organic layer was dried over anhydrous magnesium sulfate. After concentration under a reduced pressure, the residue was purified by silica column chromatography (eluent: hexane/ethyl acetate=3/1) to give the title compound (1.40 mg) as white crystals in a yield of 89%.

Workup

  1. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  2. concentrationAfter concentration under a reduced pressure
  3. customthe residue was purified by silica column chromatography (eluent: hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-4c70a4190e634427b46625d4408ba5df
Source dataset
uspto-grants-2006_04
Patent number
US07026515B2

Reaction notes

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