Triethylamine → HCID 67147970, compound

HRID 910316Notes

Reaction equation

HRID 910316 reaction equation
[C:1](Cl)(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH2:9]([O:11][C@@H:12]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:28]=[C:27]([CH2:29][NH:30][CH3:31])[S:26][CH:25]=2)=[CH:20][CH:19]=1)[C:13]([O:15][CH3:16])=[O:14])[CH3:10].C(N(CC)CC)C>O1CCCC1>[CH2:9]([O:11][C@@H:12]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:28]=[C:27]([CH2:29][N:30]([C:1](=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[CH3:31])[S:26][CH:25]=2)=[CH:20][CH:19]=1)[C:13]([O:15][CH3:16])=[O:14])[CH3:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 67340Hexanoyl chlorideHCID 67148228HCID 67148228, compound

Product 1

HCID 67147970HCID 67147970, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.18 ml (1.3 mmol) of hexanoyl chloride is added to a solution, cooled beforehand to 0° C., of 0.4 g (1.2 mmol) of methyl 2(S)-ethoxy-3-[4-(5-methylaminomethylthiophen-3-yl)phenyl]propanoate and 0.18 ml (1.3 mmol) of triethylamine in 20 ml of tetrahydrofuran. The reaction medium is stirred at room temperature for 2 hours, washed with water and extracted with ethyl acetate. The ethyl acetate phase is dried over magnesium sulfate, filtered and evaporated. The residue obtained is purified by thin-layer chromatography on silica eluted with a 70/30 heptane/ethyl acetate mixture. 0.4 g (83%) of methyl 2(S)-ethoxy-3-(4-{5-[(hexanoylmethylamino)methyl]thiophen-3-yl}phenyl)propanoate is obtained.

Workup

  1. washwashed with water
  2. extractionextracted with ethyl acetate
  3. dry with materialThe ethyl acetate phase is dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue obtained
  7. customis purified by thin-layer chromatography on silica
  8. washeluted with a 70/30 heptane/ethyl acetate mixture

Sources & evidence

ORD record
ord-69ed2ce0c9fd43beac8b1cd61d32a8f6
Source dataset
uspto-grants-2011_09
Patent number
US08022079B2

Reaction notes

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