Ethyl Acetate → HCID 15550453, compound

HRID 1596508Notes

Reaction equation

HRID 1596508 reaction equation
[CH3:1][C:2]([O:5][C:6](=[O:29])[N:7]([CH2:19][C@@H:20]([OH:28])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[N:22]=1)[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=1)([CH3:4])[CH3:3].[Sn](Cl)Cl.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>CO>[CH3:4][C:2]([O:5][C:6](=[O:29])[N:7]([CH2:19][C@@H:20]([OH:28])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[N:22]=1)[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=1)([CH3:1])[CH3:3]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24479Stannous ChlorideHCID 516892Sodium BicarbonateHCID 15550452HCID 15550452, compound

Product 1

HCID 15550453HCID 15550453, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1.00 g (2.37 mmol) of (R)-N-[2-(4-nitrophenyl)ethyl]-2-hydroxy-2-(6-chloro-2-pyridyl)ethylcarbamic acid 1,1-dimethylethyl ester in 60 mL of methanol under an atmosphere of nitrogen was added 1.35 g (7.12 mmol) of tin(II) chloride. The mixture was heated at reflux for 5 h then cooled to room temperature. Saturated aqueous sodium bicarbonate solution was added followed by ethyl acetate. The resulting emulsion was filtered through Celite and the organic phase separated. The aqueous phase was re-extracted twice with ethyl acetate. The combined organic phase was washed twice with water, brine, dried over magnesium sulfate and the solvent removed in vacuo. Biotage chromatography (40M column, 30, 35% ethyl acetate-hexanes) afforded 510 mg (55%) of (R)-N-[2-(4-aninophenyl)ethyl]-2-hydroxy-2-(6-chloro-2-pyridyl)ethylcarbamic acid 1,1-dimethylethyl ester.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 5 h
  3. filtrationThe resulting emulsion was filtered through Celite
  4. customthe organic phase separated
  5. extractionThe aqueous phase was re-extracted twice with ethyl acetate
  6. washThe combined organic phase was washed twice with water, brine
  7. dry with materialdried over magnesium sulfate
  8. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-673e27979c2b4bbab00c5ddbea68a08d
Source dataset
uspto-grants-2001_09
Patent number
US06291491B1

Reaction notes

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