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

HRID 2300658Notes

Reaction equation

HRID 2300658 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 dichloroethane (3×50 mL). The combined extracts were dried (Na2SO4) and evaporated to afford a yellow oil (3.82 g; 49%). 1H-NMR (CDCl3) δ7.26 (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 dichloroethane (3×50 mL)
  8. dry with materialThe combined extracts were dried (Na2SO4)
  9. customevaporated
  10. customto afford a yellow oil (3.82 g; 49%)

Sources & evidence

ORD record
ord-48e3ed0911b946cfbc09d43f69cdb148
Source dataset
uspto-grants-2002_12
Patent number
US06498174B1

Reaction notes

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