Hydrochloric Acid → HCID 69205592, compound

HRID 30660Notes

Reaction equation

HRID 30660 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]([O:21]CC)=O)=[CH:14][CH:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:24]([Mg]Br)[CH3:25].Cl.O1CC[CH2:31][CH2:30]1>>[CH2:30]([C:19]([OH:21])([CH2:24][CH3:25])[CH2:18][C:15]1[CH:14]=[CH:13][C:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:17][CH:16]=1)[CH3:31]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 67375141HCID 67375141, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 69205592HCID 69205592, compound

Procedure

To a mixture of ethyl (4-{[(benzyloxy)carbonyl]amino}phenyl)acetate (15.3 g) and tetrahydrofuran (100 mL) was added dropwise 1 M ethyl magnesium bromide (1 M tetrahydrofuran solution, 500 g) at 0° C. The reaction mixture was stirred at room temperature for 15 hrs. 1N Hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give benzyl 4-(2-ethyl-2-hydroxybutyl)phenylcarbamate as colorless crystals from a fraction eluted with hexane-ethyl acetate (2:1-1:1, v/v). Recrystallization thereof from ethyl acetate-hexane gave colorless prism crystals (6.86 g, yield 43%). melting point: 99-100° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-265febaad9564ec5b597293b802dd073
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Reaction notes

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