Sodium Hydroxide → HCID 57467284, compound

HRID 1044514Notes

Reaction equation

HRID 1044514 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:33]=[C:34]([F:36])[CH:35]=1)[CH2:5][CH:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:16][CH2:17][CH2:18][NH:19][S:20]([CH2:23][CH:24]3[CH2:26][CH2:25]3)(=[O:22])=[O:21])[CH:14]=2)[CH2:9][CH2:8][CH:7]1[NH:27][C:28](=O)OCC.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+].CC(O)C.Cl>C1COCC1.C(Cl)Cl>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:33]=[C:34]([F:36])[CH:35]=1)[CH2:5][CH:6]1[C:15]2[CH:14]=[C:13]([O:16][CH2:17][CH2:18][NH:19][S:20]([CH2:23][CH:24]3[CH2:26][CH2:25]3)(=[O:22])=[O:21])[CH:12]=[CH:11][C:10]=2[CH2:9][CH2:8][CH:7]1[NH:27][CH3:28]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 21912024Isopropanol hydrochlorideHCID 57471299HCID 57471299, compound

Product 1

HCID 57467284HCID 57467284, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

The synthesis was performed starting from ethyl 1-(3-chloro-5-fluorobenzyl)-7-(2-(cyclopropylmethylsulfonamido)ethoxy)-1,2,3,4-tetrahydronaphthalen-2-ylcarbamate (synthesized in analogy to example 3), which was dissolved in THF (50 ml), after which LiAlH4 was added at room temperature and the mixture was stirred for 8 h under reflux. Addition of 2N aqueous NaOH, extraction with CH2Cl2, washing of the organic layers with saturated NaHCO3 solution and saturated NaCl solution and evaporation of the solvent gave a residue that was treated with iPrOH/HCl after which the product precipitated. After filtration a white salt (134 mg, 39%) was obtained.

Workup

  1. temperatureunder reflux
  2. washwashing of the organic layers with saturated NaHCO3 solution and saturated NaCl solution and evaporation of the solvent
  3. customgave a residue that
  4. customprecipitated
  5. filtrationAfter filtration a white salt (134 mg, 39%)
  6. customwas obtained

Sources & evidence

ORD record
ord-3df1eae3499a4fbd82fb1c69c005f855
Source dataset
uspto-grants-2013_10
Patent number
US08563617B2

Reaction notes

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