Hydrochloric Acid → (4-{2-[(4-Butyl-benzyl)-methanesulfonyl-amino]-ethyl}-phenyl)-acetic acid methyl ester

HRID 890731Notes

Reaction equation

HRID 890731 reaction equation
[CH3:1][O:2][C:3](=[O:18])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][NH:13][S:14]([CH3:17])(=[O:16])=[O:15])=[CH:7][CH:6]=1.Br[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][CH2:29][CH3:30])=[CH:23][CH:22]=1.C([O-])([O-])=O.[K+].[K+].Cl>CCOC(C)=O.C(#N)C>[CH3:1][O:2][C:3](=[O:18])[CH2:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:11][CH2:12][N:13]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][CH2:29][CH3:30])=[CH:23][CH:22]=2)[S:14]([CH3:17])(=[O:15])=[O:16])=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 121508404-Butylbenzyl BromideHCID 23594256[4-[2-Methanesulfonylamino-ethyl]-phenyl]-acetic acid methyl ester

Product 1

HCID 57035818(4-{2-[(4-Butyl-benzyl)-methanesulfonyl-amino]-ethyl}-phenyl)-acetic acid methyl ester

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of [4-[2-methanesulfonylamino-ethyl]-phenyl]-acetic acid methyl ester (38 mg, 0.14 mmol), 1-bromomethyl-4-butylbenzene (35 mg, 0.15 mmol), K2CO3 (25 mg, 0.182 mmol) and acetonitrile was heated at reflux for 1 h. Aqueous HCl (2 mL, 1N) and EtOAc (30 mL) were added to the reaction. The organic solution was dried with MgSO4, filtered, and concentrated in vacuo. The product was purified by flash chromatography (30% EtOAc/hexanes) to afford the title compound of Step A. 1H NMR (400 MHz, CDCl3) δ 7.28–7.05 (m, 8H), 4.37 (s, 2H), 3.65 (s, 3H), 3.58 (s, 2H), 3.26 (t, 2H), 2.77 (t, 2H), 2.69 (s, 3H), 2.60 (t, 2H), 1.59 (m, 2H), 1.37 (m, 2H), 0.94 (t, 3H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 h
  3. dry with materialThe organic solution was dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe product was purified by flash chromatography (30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-7574ac421fa24986a1209cc909f44361
Source dataset
uspto-grants-2006_02
Patent number
US06998423B2

Reaction notes

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