Sodium Bicarbonate → N-(4-(4-(Ethyl(6-acetoxy-6-methylheptyl)amino)-1-hydroxybutyl)phenyl)methanesulfonamide

HRID 1654297Notes

Reaction equation

HRID 1654297 reaction equation
[CH2:1]([NH:3][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].[C:20]([O:23][C:24]([CH3:32])([CH3:31])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]Br)(=[O:22])[CH3:21].C(=O)(O)[O-].[Na+]>C(#N)C>[CH2:1]([N:3]([CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][C:24]([O:23][C:20](=[O:22])[CH3:21])([CH3:31])[CH3:32])[CH2:4][CH2:5][CH2:6][CH:7]([C:9]1[CH:10]=[CH:11][C:12]([NH:15][S:16]([CH3:19])(=[O:17])=[O:18])=[CH:13][CH:14]=1)[OH:8])[CH3:2]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 10779588N-(4-(4-(ethylamino)-1-hydroxybutyl)phenyl)methanesulfonamideHCID 200801086-Acetoxy-1-bromo-6-methylheptane

Product 1

HCID 15294456N-(4-(4-(Ethyl(6-acetoxy-6-methylheptyl)amino)-1-hydroxybutyl)phenyl)methanesulfonamideYield 68.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A stirred mixture of the product from Example 7, Step II (1.5 g, 0.00524 mol), the product from Step V above 1.45 g, 0.00576 mol), sodium bicarbonate (0.88 g, 0.0105 mol) and acetonitrile (45 ml) was warmed at 90°-95°, under nitrogen for 6 hours and kept at ambient temperature for 11 hours. It was then filtered. The filtrate was concentrated and the residue chromatographed on silica gel with 0.5% NH4OH-6% MeOH--CH2Cl2 to give 1.63 g of the titled compound which is a compound of Formula I'. The high resolution mass spectrum had m/z 456 (M+). Theory for C23H40N2O5S: 456.2658; measured: 456.2650.

Workup

  1. filtrationIt was then filtered
  2. concentrationThe filtrate was concentrated
  3. customthe residue chromatographed on silica gel with 0.5% NH4OH-6% MeOH

Sources & evidence

ORD record
ord-66c17db0613c49e3bdd8aa1b17841d4e
Source dataset
uspto-grants-1995_04
Patent number
US05405997

Reaction notes

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