Triethylamine → 4-{1-ethyl-1-[4-(2-hydroxy-3,3-dimethylbutoxy)-3-methylphenyl]propyl}-N-(2-methanesulfonylethyl)-2-methylbenzamide

HRID 230815Notes

Reaction equation

HRID 230815 reaction equation
[OH:1][CH:2]([C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([C:16]2[CH:24]=[CH:23][C:19]([C:20](O)=[O:21])=[C:18]([CH3:25])[CH:17]=2)([CH2:14][CH3:15])[CH2:12][CH3:13])=[CH:7][C:6]=1[CH3:26].Cl.[NH2:32][CH2:33][CH2:34][S:35]([CH3:38])(=[O:37])=[O:36].C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC.CCN=C=NCCCN(C)C>C(Cl)Cl>[CH2:12]([C:11]([C:16]1[CH:24]=[CH:23][C:19]([C:20]([NH:32][CH2:33][CH2:34][S:35]([CH3:38])(=[O:37])=[O:36])=[O:21])=[C:18]([CH3:25])[CH:17]=1)([C:8]1[CH:9]=[CH:10][C:5]([O:4][CH2:3][CH:2]([OH:1])[C:27]([CH3:30])([CH3:28])[CH3:29])=[C:6]([CH3:26])[CH:7]=1)[CH2:14][CH3:15])[CH3:13]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 103643684-{1-[4-(3,3-Dimethyl-2-hydroxybutoxy)-3-methylphenyl]-1-ethylpropyl}-2-methylbenzoic acidHCID 17749886Ethanamine, 2-(methylsulfonyl)-, hydrochloride (1:1)

Product 1

HCID 577634394-{1-ethyl-1-[4-(2-hydroxy-3,3-dimethylbutoxy)-3-methylphenyl]propyl}-N-(2-methanesulfonylethyl)-2-methylbenzamideYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 4-(1-{4-[2-(hydroxy)-3,3-dimethyl-butoxy]-3-methylphenyl}-1-ethylpropyl)-2-methylbenzoic acid, Example 1, (0.53 g, 1.29 mmol), 2-aminoethylmethylsulfone hydrochloride (0.21 g, 1.29 mmol), HOBt (0.19 g, 1.43 mmol), Et3N (0.72 mL, 5.19 mmol) and CH2Cl2 (10 mL) is added EDCI (0.249 g, 1.29 mmol) and stirred overnight. The reaction is diluted with CH2Cl2 (50 mL), washed with 1M HCl (2×30 mL), H2O (20 mL), satd NaHCO3 (2×20 mL), and brine (20 mL). The organic layer is MgSO4 dried, concentrated, and chromatographed (75% EtOAc/Hex) to give the title compound (0.51 g, 76%).

Workup

  1. washwashed with 1M HCl (2×30 mL), H2O (20 mL), satd NaHCO3 (2×20 mL), and brine (20 mL)
  2. customdried
  3. concentrationconcentrated
  4. customchromatographed (75% EtOAc/Hex)

Sources & evidence

ORD record
ord-e4c1739ea4a540be87e4260d5affef8f
Source dataset
uspto-grants-2009_07
Patent number
US07566803B2

Reaction notes

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