tert-Butanol → [2-(4-Fluoro-3-methoxyphenyl)ethyl]carbamic acid t-butyl ester

HRID 1351260Notes

Reaction equation

HRID 1351260 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9]C(O)=O)=[CH:4][C:3]=1[O:13][CH3:14].C([N:17]([CH2:20]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:29])C=CC=CC=1.[C:39]([OH:43])([CH3:42])([CH3:41])[CH3:40]>>[C:39]([O:43][C:20](=[O:29])[NH:17][CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([O:13][CH3:14])[CH:4]=1)([CH3:42])([CH3:41])[CH3:40]

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 210986063-(4-Fluoro-3-methoxyphenyl)propanoic acid

Product 1

HCID 69415384[2-(4-Fluoro-3-methoxyphenyl)ethyl]carbamic acid t-butyl ester

Procedure

3-(4-Fluoro-3-methoxyphenyl)propionic acid (1.98 g), triethylamine (1.67 mL) and diphenylphosphoryl azide (2.59 mL) in t-butanol (20 mL) were heated at 95 to 100° C. for 5 hours. After cooling the reaction solution, the residue that was obtained upon removing the solvent by evaporation was purified by silica gel column chromatography (hexane/ethyl acetate), and the title compound (1.59 g) was obtained as a colorless oily matter.

Workup

  1. temperatureAfter cooling the reaction solution
  2. customthe residue that was obtained
  3. customupon removing the solvent
  4. customby evaporation
  5. customwas purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-7670b81d2cca460c868203873a43effd
Source dataset
uspto-grants-2007_05
Patent number
US07217723B2

Reaction notes

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