Triethylamine → HCID 18678876, compound

HRID 1634704Notes

Reaction equation

HRID 1634704 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]([CH2:7][CH2:8][NH:9][CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:5][CH:4]=1.[N+]([C:21]1[CH:22]=[C:23]([S:27](Cl)(=[O:29])=[O:28])[CH:24]=[CH:25][CH:26]=1)([O-])=O.[CH2:31]([N:33](CC)CC)C>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][CH2:8][N:9]([S:27]([C:23]2[CH:24]=[CH:25][C:26]([C:31]#[N:33])=[CH:21][CH:22]=2)(=[O:29])=[O:28])[CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 84763-Nitrobenzenesulfonyl chlorideHCID 18678923HCID 18678923, compound

Product 1

HCID 18678876HCID 18678876, compoundYield 61.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of methyl acrylate (6.0 g, 69.7 mmol) and p-methoxyphenethyl amine (10.5 g, 69.7 mmol) in anhydrous methanol (88 mL) was refluxed for 3 days and then was concentrated to give methyl 3-[(4-methoxyphenethyl)amino]-propionate (16.2 g). To a solution of methyl 3-[(4-methoxyphenethyl)amino]-propionate (3.0 g, 12.6 mmol) in anhydrous methylene chloride (35 mL) was added 3-nitrobenzenesulfonyl chloride (2.8 g, 12.6 mmol), followed by triethylamine (2.6 g, 25.3 mmol). After stirring for 18 h at room temperature, the mixture was quenched with 1 N HCl solution (150 mL) and extracted with methylene chloride (100 mL). Combined organic layers was washed successively with 1 N HCl solution (100 mL) and brine, dried over MgSO4, filtered, and concentrated. The crude product was purified by silica gel flash chromatography (2.5/1 to 2/1: hexanes/EtOAc) to provide methyl 3-[(4-methoxyphenethyl)-(4-cyanobenzenesulfonyl)-amino]-propionate (3.28 g, 7.8 mmol).

Workup

  1. customthe mixture was quenched with 1 N HCl solution (150 mL)
  2. extractionextracted with methylene chloride (100 mL)
  3. washCombined organic layers was washed successively with 1 N HCl solution (100 mL) and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by silica gel flash chromatography (2.5/1 to 2/1: hexanes/EtOAc)

Sources & evidence

ORD record
ord-c3a786e7393c4a089b141e726bc69685
Source dataset
uspto-grants-2003_01
Patent number
US06506936B1

Reaction notes

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