Diethyl Ether → 2-(4-(2-(Phenylmethyloxycarbonylamino)ethyl)phenoxy)-2-methylbutanoic Acid

HRID 1058932Notes

Reaction equation

HRID 1058932 reaction equation
[C:1]1([CH2:7][O:8][C:9]([NH:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(Cl)Cl.[OH-:25].[Na+].[CH3:27][CH2:28]OCC.C[C:33](=[O:36])[CH2:34][CH3:35]>>[C:1]1([CH2:7][O:8][C:9]([NH:11][CH2:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([O:20][C:34]([CH3:35])([CH2:27][CH3:28])[C:33]([OH:36])=[O:25])=[CH:18][CH:19]=2)=[O:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 5

HCID 3283Diethyl EtherHCID 6212ChloroformHCID 6569Methyl Ethyl Ketone2×HCID 14798Sodium HydroxideHCID 14103856Benzyl [2-(4-hydroxyphenyl)ethyl]carbamate

Product 1

HCID 186694352-(4-(2-(Phenylmethyloxycarbonylamino)ethyl)phenoxy)-2-methylbutanoic Acid

Conditions

Temperature
30 °C

Procedure

A solution of 4-(2-(phenylmethyloxycarbonylamino)ethyl)phenol (5.74 g; 21.16 mmole) in 2-butanone (17 mL) and chloroform (6 g) was added dropwise to a mixture of sodium hydroxide (9.0 g; 225 mmole) and 2-butanone (67 mL) whilst keeping the reaction temperature below 30° C. The mixture was allowed to stir at 30° C. for 4 h. Ether (100 mL) was added and the resultant solid was collected by filtration and washed with ether (100 mL). The solid was dissolved in water (70 mL) and any residual ether removed by evaporation. 1N Hydrochloric acid was added to adjust the pH to 1, and the resulting oil was extracted with dichloromethane (3×50 mL). The combined extracts were dried (Na2SO4) and evporated to afford a yellow oil (3.82 g; 49%). 1H-NMR (CDCl3) δ 7.26 (s, 5H), 7.09 (d, 2H, J=7.9 Hz), 6.88 (d, 2H, J=8.4 Hz), 5.09 (s, 2H), 4.75 (br s, 1H), 3.42-3.44 (m, 2H), 2.75 (t, 2H, J=6.7 Hz), 1.92-2.00 (m, 2H), 1.47 (s, 3H), 1.04 (t, 3H, J=2.6 Hz). Mass spectrometry ES+, m/e (M+H)+=372.

Workup

  1. customthe reaction temperature below 30° C
  2. filtrationthe resultant solid was collected by filtration
  3. washwashed with ether (100 mL)
  4. dissolutionThe solid was dissolved in water (70 mL)
  5. customany residual ether removed by evaporation
  6. addition1N Hydrochloric acid was added
  7. extractionthe resulting oil was extracted with dichloromethane (3×50 mL)
  8. dry with materialThe combined extracts were dried (Na2SO4)
  9. customto afford a yellow oil (3.82 g; 49%)

Sources & evidence

ORD record
ord-bf79c1dd1d3543c38d62ef3069e6df4b
Source dataset
uspto-grants-2003_02
Patent number
US06518290B1

Reaction notes

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