Octanoyl chloride → HCID 66591604, compound

HRID 1092300Notes

Reaction equation

HRID 1092300 reaction equation
[CH2:1]([O:5][C:6]1[CH:7]=[C:8]([CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])[CH:9]=[CH:10][C:11]=1[C:12]1[CH:16]=[C:15](CNC)[S:14][CH:13]=1)[CH2:2][CH2:3][CH3:4].[CH3:26][N:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31]N=1)[CH3:28].[C:35](Cl)(=O)[CH2:36][CH2:37]CCCCC.C(=O)([O-])[OH:46].[Na+]>ClCCl.C(N(CC)CC)C>[CH2:1]([O:5][C:6]1[CH:7]=[C:8]([CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])[CH:9]=[CH:10][C:11]=1[C:12]1[CH:16]=[C:15]([CH2:26][N:27]([CH3:28])[C:29](=[O:46])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:35][CH2:36][CH3:37])[S:14][CH:13]=1)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 8124Octanoyl chlorideHCID 218852-DimethylaminopyridineHCID 516892Sodium BicarbonateHCID 66591263HCID 66591263, compound

Product 1

HCID 66591604HCID 66591604, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

1.07 g of methyl 3-[3-butoxy-4-(5-methylaminomethylthiophen-3-yl)phenyl]propionate are dissolved in 20 mL of dichloromethane, and 1.25 mL of triethylamine are added, along with 36 mg of dimethylaminopyridine. 318 mg of octanoyl chloride are added. The reaction mixture is stirred for 12 hours at room temperature. After hydrolyzing the reaction with sodium hydrogen carbonate solution and then extracting with ethyl acetate and evaporating off the solvents, a crude product is obtained, which is chromatographed on silica gel (eluent=7/3 heptane/ethyl acetate). 432 mg of methyl 3-(3-butoxy-4-{5-[(methyloctanoylamino)methyl]thiophen-3-yl}phenyl)propionate are obtained. Yield=81%.

Workup

  1. extractionextracting with ethyl acetate
  2. customevaporating off the solvents
  3. customa crude product is obtained
  4. customwhich is chromatographed on silica gel (eluent=7/3 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-4990718ca1ca47cfba2269518593bc29
Source dataset
uspto-grants-2012_03
Patent number
US08129416B2

Reaction notes

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