Potassium Carbonate → HCID 59363840, compound

HRID 1430621Notes

Reaction equation

HRID 1430621 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([OH:14])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:22]([O:24][C:25](=[O:30])[C:26](Br)([CH3:28])[CH3:27])[CH3:23]>CN(C=O)C.CCOC(C)=O>[CH2:22]([O:24][C:25](=[O:30])[C:26]([O:14][C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:15])[CH:9]=1)([CH3:28])[CH3:27])[CH3:23]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 312485tert-butyl N-(3-hydroxyphenyl)carbamate

Product 1

HCID 59363840HCID 59363840, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of (3-Hydroxy-phenyl)-carbamic acid tert-butyl ester (2.4 g, 11.4 mmol) in 5 ml of dry DMF, anhydrous potassium carbonate (7.9 g, 57.416 mmol) was added. The mixture stirred for 5-10 minutes, added ethyl-2-bromo-isobutyrate (4.5 g, 22.9 mmol). The resulting mixture was heated at 70° C. for 12 hours. Upon completion (˜25 h), the solution was diluted with EtOAc (25 ml) and washed with saturated NH4Cl (5 ml). The aqueous layer was then extracted for two additional times with EtOAc (10 ml) and the combined organic fractions were washed with brine (2×5 ml). The solution was then dried over Na2SO4 and concentrated to give brown oil. Purification on silica gel (hexanes/acetone) yielded 1.8 g (49%). 1H-NMR (400 MHz, CDCl3): δ 1H NMR (400 MHz, CDCl3): 1.26 (t, J=7.2 Hz, 3H), 1.50 (s, 9H), 1.59 (s, 6H), 6.43 (s, 1H), 6.47-6.50 (m, 1H), 6.96 (t, J=8.4 Hz, 2H), 7.11 (t, J=8.0, 1H).

Workup

  1. washwashed with saturated NH4Cl (5 ml)
  2. extractionThe aqueous layer was then extracted for two additional times with EtOAc (10 ml)
  3. washthe combined organic fractions were washed with brine (2×5 ml)
  4. dry with materialThe solution was then dried over Na2SO4
  5. concentrationconcentrated
  6. customto give brown oil
  7. customPurification on silica gel (hexanes/acetone)
  8. customyielded 1.8 g (49%)

Sources & evidence

ORD record
ord-ab50958bb875469abc349bd655366117
Source dataset
uspto-grants-2015_01
Patent number
US08940900B2

Reaction notes

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