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Potassium sodium tartarate → N-(4-(4-(Ethyl(4,4-dimethylpentyl)amino)-1-hydroxybutyl)phenyl)methanesulfonamide

HRID 1654294
Notes
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Reaction equation

HRID 1654294 reaction equation
[CH2:1]([N:3]([C:20](=O)[CH2:21][CH2:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:4][CH2:5][CH2:6][CH:7]([C:9]1[CH:14]=[CH:13][C:12]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])=[CH:11][CH:10]=1)[OH:8])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C1COCC1>[CH2:1]([N:3]([CH2:20][CH2:21][CH2:22][C:23]([CH3:24])([CH3:26])[CH3:25])[CH2:4][CH2:5][CH2:6][CH:7]([C:9]1[CH:10]=[CH:11][C:12]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])=[CH:13][CH:14]=1)[OH:8])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 9855836Potassium sodium tartarateHCID 20080099N-(4-(4-(ethyl(4,4-dimethylpentanoyl)amino)-1-hydroxybutyl)phenyl)methanesulfonamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 15294455N-(4-(4-(Ethyl(4,4-dimethylpentyl)amino)-1-hydroxybutyl)phenyl)methanesulfonamide

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
3×

Procedure

A solution of the product from Step I (4.4 g, 0.0115 mol) in THF (46.4 ml) was added dropwise during 45 minutes, under nitrogen to a stirred, ice cold mixture of a 1M solution of LiAlH4 in THF (24.0 ml) and THF (24 ml). The mixture was kept in the ice bath for 45 minutes and then treated slowly with a saturated aqueous solution of potassium sodium tartrate (24.4 ml). This mixture was stirred for 30 minutes and extracted with EtOAc. The extracts were washed with water and brine, dried (MgSO4) and concentrated. The residue was chromatographed on silica gel with 5-10% MeOH--CHCl3. The product was dissolved in Et2O, washed with NaHCO3, dried (MgSO4) and concentrated to give 2.96 of the titled compound. The FAB mass spectrum had m/z 385 (M+H)+. Theory for C20H37N2O3S: 385.2525; measured.: 385.2546.

Workup

  1. extractionextracted with EtOAc
  2. washThe extracts were washed with water and brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica gel with 5-10% MeOH
  6. dissolutionThe product was dissolved in Et2O
  7. washwashed with NaHCO3
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-a2f269729b65413ca26f17e89f1a5470
Source dataset
uspto-grants-1995_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05405997

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes