Ammonium Chloride → HCID 86625215, compound

HRID 1010897Notes

Reaction equation

HRID 1010897 reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][C@H:8]([C:10]1[CH:15]=[CH:14][C:13]([CH:16]=[O:17])=[CH:12][CH:11]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2].[CH2:19]([Mg]Cl)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[Cl-].[NH4+]>O1CCCC1>[OH:17][CH:16]([C:13]1[CH:14]=[CH:15][C:10]([C@@H:8]([NH:7][C:6](=[O:18])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH3:9])=[CH:11][CH:12]=1)[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 89479126HCID 89479126, compoundHCID 178418336HCID 178418336, compound

Product 1

HCID 86625215HCID 86625215, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

70 mg of the compound [15-1] was dissolved in 5 mL of tetrahydrofuran and cooled to 0° C. Thereafter, 300 μL of benzylmagnesium chloride (2.0M tetrahydrofuran solution) was added thereto, and the mixture was stirred overnight while gradually heating back to room temperature. To the reaction solution was added a saturated aqueous solution of ammonium chloride, and the solution was extracted with ethyl acetate. The obtained organic layer was washed with water and saturated brine in that order, and dried over anhydrous sodium sulfate. The insolubles were filtered, the filtrate was concentrated under reduced pressure, and then the resulting residue was purified by preparative thin-layer chromatography, to obtain 11 mg of the tert-butyl {(1S)-1-[4-(1-hydroxy-2-phenylethyl) phenyl]ethyl}carbamate [16-1] (hereinafter, referred to as the compound [16-1]) as a colorless oily product.

Workup

  1. temperaturewhile gradually heating back to room temperature
  2. extractionthe solution was extracted with ethyl acetate
  3. washThe obtained organic layer was washed with water and saturated brine in that order
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationThe insolubles were filtered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customthe resulting residue was purified by preparative thin-layer chromatography

Sources & evidence

ORD record
ord-a7d51c1afeef4af5822e4cbb8601e647
Source dataset
uspto-grants-2011_07
Patent number
US07977336B2

Reaction notes

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