Octylmethylamine → 2-[(4-Methoxy-benzenesulfonyl)-methyl-amino]-3-methyl-5-[2-(methyl-octyl-carbamoyl)-vinyl]-benzoic acid methyl ester

HRID 583355

Reaction equation

HRID 583355 reaction equation
[CH3:1][O:2][C:3](=[O:29])[C:4]1[CH:9]=[C:8]([CH:10]=[CH:11][C:12](O)=[O:13])[CH:7]=[C:6]([CH3:15])[C:5]=1[N:16]([S:18]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)(=[O:20])=[O:19])[CH3:17].[CH3:30][NH:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]>C1COCC1>[CH3:1][O:2][C:3](=[O:29])[C:4]1[CH:9]=[C:8]([CH:10]=[CH:11][C:12](=[O:13])[N:31]([CH3:30])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH:7]=[C:6]([CH3:15])[C:5]=1[N:16]([S:18]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)(=[O:20])=[O:19])[CH3:17]

Participants

4

Reactant 2

HCID 75538OctylmethylamineHCID 700551955-(2-Carboxy-vinyl)-2-[(4-methoxy-benzenesulfonyl)-methyl-amino]-3-methyl-benzoic acid methyl ester

Product 1

HCID 700537552-[(4-Methoxy-benzenesulfonyl)-methyl-amino]-3-methyl-5-[2-(methyl-octyl-carbamoyl)-vinyl]-benzoic acid methyl esterYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 182.6 mg (0.43 mmol) of the product of Example 204, 183 mg of molecular sieves and 105.8 mg (0.65 mmol) of 1,1'-dicyclohexylcarbodiimidazole in 4 ml THF was stirred for 1 h under nitrogen. A solution of N-methyloctylamine in 0.5 ml THF was then added to the reaction and the mixture was stirred for 18 hr at room temperature. The resulting mixture was filtered and the filtrate was diluted with ethyl acetate, washed with water and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was chromatographed on silica gel eluting with EtOAc/Hexane (1:1) to provide 200 mg (84%) of the desired product as a colorless oil. Electrospray Mass Spec 545(M+H).

Workup

  1. stirringthe mixture was stirred for 18 hr at room temperature
  2. filtrationThe resulting mixture was filtered
  3. additionthe filtrate was diluted with ethyl acetate
  4. washwashed with water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was chromatographed on silica gel eluting with EtOAc/Hexane (1:1)

Sources & evidence

ORD record
ord-925866f7b42b4849b1ffa781ad5ca878
Source dataset
uspto-grants-1999_07
Patent number
US05929097

Linked notes

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