Tetrahydrofuran → 3-Ethoxy-3-oxo-2-{4-[2-(2-oxo-1,3-benzoxazol-3(2H)-yl)ethoxy]benzyl}propanoic acid

HRID 896484Notes

Reaction equation

HRID 896484 reaction equation
[O:1]=[C:2]1[N:6]([CH2:7][CH2:8][O:9][C:10]2[CH:27]=[CH:26][C:13]([CH2:14][CH:15]([C:21]([O:23]CC)=[O:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:12][CH:11]=2)[C:5]2[CH:28]=[CH:29][CH:30]=[CH:31][C:4]=2[O:3]1.O1CCCC1.[OH-].[Na+]>C(O)C>[CH2:19]([O:18][C:16](=[O:17])[CH:15]([CH2:14][C:13]1[CH:12]=[CH:11][C:10]([O:9][CH2:8][CH2:7][N:6]2[C:5]3[CH:28]=[CH:29][CH:30]=[CH:31][C:4]=3[O:3][C:2]2=[O:1])=[CH:27][CH:26]=1)[C:21]([OH:23])=[O:22])[CH3:20]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 10159558Diethyl 2-{4-[2-(2-oxo-1,3-benzoxazol-3(2H)-yl)ethoxy]benzyl}malonate

Product 1

HCID 101790283-Ethoxy-3-oxo-2-{4-[2-(2-oxo-1,3-benzoxazol-3(2H)-yl)ethoxy]benzyl}propanoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Dissolve the compound obtained in Example 2 (0.5 g) in absolute ethanol (6.5 ml) and add tetrahydrofuran (2 ml). Subsequently, cool the reaction mixture using an ice bath and add 2N sodium hydroxide (0.7 ml). Stir magnetically for 18 hours at ambient temperature. Remove the absolute ethanol/tetrahydrofuran mixture by evaporation under reduced pressure. Take up the resulting residue in water and extract twice with 50 ml of ether each time. Acidify the aqueous phase with a 6N hydrochloric acid solution until a pH of 1 is obtained, then extract twice with 50 ml of ether each time. Dry the organic phase over magnesium sulphate and remove the ether by evaporation under reduced pressure.

Workup

  1. temperatureSubsequently, cool the reaction mixture
  2. customRemove the absolute ethanol/tetrahydrofuran mixture
  3. customby evaporation under reduced pressure
  4. extractionextract twice with 50 ml of ether each time
  5. customis obtained
  6. extractionextract twice with 50 ml of ether each time
  7. dry with materialDry the organic phase over magnesium sulphate
  8. customremove the ether
  9. customby evaporation under reduced pressure

Sources & evidence

ORD record
ord-46d3b8e4999f48e5a8504d0dd0554259
Source dataset
uspto-grants-2005_07
Patent number
US06919362B2

Reaction notes

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