Triethylamine → HCID 18339255, compound

HRID 2298721Notes

Reaction equation

HRID 2298721 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH2:16][CH2:17][C:18]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=2)=[O:19])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].Br.[Br:32][CH2:33][CH2:34][NH2:35].C(N(CC)CC)C>C1COCC1>[Br:32][CH2:33][CH2:34][NH:35][S:27]([C:24]1[CH:25]=[CH:26][C:21]([NH:20][C:18](=[O:19])[CH2:17][CH2:16][C:7]2[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:10]([OH:11])=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH:8]=2)=[CH:22][CH:23]=1)(=[O:29])=[O:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27742172-Bromoethylamine hydrobromideHCID 18377846HCID 18377846, compound

Product 1

HCID 18339255HCID 18339255, compoundYield 51.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred suspension of 4-[3-(3,5-di-tert-butyl-4-hydroxy-phenyl)-propionylamino]-benzenesulfonyl chloride (4.38 g, 0.0097 mol) and 2-bromoethylamine hydrobromide (2.11 g, 0.0103 mol) in THF (30 g) at 0-2° C. under nitrogen was added dropwise a solution of triethylamine (2.01 g, 0.0199 mol) in THF (9 g). When addition was complete, the reaction mixture was stirred at room temperature for 20 hours. The reaction mixture was filtered and the filtrate was spin evaporated in vacuo. The residue was chromatographed over silica (toluene/acetone 75:25) to give 2.7 g of N-[4-(2-bromoethylsulfamoyl)-phenyl]-3-(3,5-di-tert-butyl -4-hydroxy-phenyl)-propionamide as a white crystalline solid, mp 153-155° C.

Workup

  1. additionWhen addition
  2. filtrationThe reaction mixture was filtered
  3. customevaporated in vacuo
  4. customThe residue was chromatographed over silica (toluene/acetone 75:25)

Sources & evidence

ORD record
ord-6985840be8f14ba08b866598d2e3bf7c
Source dataset
uspto-grants-2002_12
Patent number
US06495125B2

Reaction notes

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