Sodium Hydroxide → HCID 22261864, compound

HRID 1610491Notes

Reaction equation

HRID 1610491 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH:15]3[O:19]C(=O)[NH:17][CH:16]3[CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([O:28][C:29]([F:34])([F:33])[CH:30]([F:32])[F:31])[CH:23]=3)=[CH:11][CH:10]=2)=[CH:4][C:3]=1[CH2:35][CH3:36].[OH-].[Na+]>C(O)C>[NH2:17][CH:16]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([O:28][C:29]([F:34])([F:33])[CH:30]([F:32])[F:31])[CH:23]=1)[CH:15]([C:12]1[CH:13]=[CH:14][C:9]([O:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([CH2:35][CH3:36])[CH:4]=2)=[CH:10][CH:11]=1)[OH:19]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22261492HCID 22261492, compound

Product 1

HCID 22261864HCID 22261864, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (4RS,5SR)-5-(4-((4-chloro-3-ethylphenyl)oxy)phenyl)-4-((3-((1,1,2,2-tetrafluoroethyl)oxy)phenyl)methyl)-1,3-oxazolidin-2-one (4.3 g, 8.21 mmol) in ethanol (20 ml) was added 8N aqueous sodium hydroxide solution (5.13 ml, 41.1 mmol), and the mixture was heated under reflux for 4 hrs. The reaction solution was concentrated, diluted with water (100 ml), and extracted with ethyl acetate (100 ml×2). The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure to give (1RS,2SR)-2-amino-1-(4-((4-chloro-3-ethylphenyl)oxy)phenyl)-3-(3-((1,1,2,2-tetrafluoroethyl)oxy)phenyl)-1-propanol (3.64 g, 89%) as a colorless oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hrs
  3. concentrationThe reaction solution was concentrated
  4. additiondiluted with water (100 ml)
  5. extractionextracted with ethyl acetate (100 ml×2)
  6. washThe extract was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-b6d69fdbddc847f4a1a443131bc424c4
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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