2-Furancarbonyl chloride → HCID 9934955, compound

HRID 380331Notes

Reaction equation

HRID 380331 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[C:4]([N:16]2[CH2:21][CH2:20][NH:19][C@H:18]([C:22](=[O:28])[NH:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:17]2)[N:3]=1.C(N(C(C)C)CC)(C)C.[O:38]1[CH:42]=[CH:41][CH:40]=[C:39]1[C:43](Cl)=[O:44]>ClCCl>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[C:4]([N:16]2[CH2:21][CH2:20][N:19]([C:43]([C:39]3[O:38][CH:42]=[CH:41][CH:40]=3)=[O:44])[C@H:18]([C:22](=[O:28])[NH:23][C:24]([CH3:25])([CH3:27])[CH3:26])[CH2:17]2)[N:3]=1

Participants

5

Reactant 3

HCID 682422-Furancarbonyl chlorideHCID 81531DiisopropylethylamineHCID 10739024HCID 10739024, compound

Product 1

HCID 9934955HCID 9934955, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 0.243 g of the above intermediate 3A, 0.17 ml of diisopropylethylamine, 0.08 ml of 2-furoyl chloride in 10 ml of dichloromethane was stirred at room temperature for 10 hours. The solution was diluted with dichloromethane (10 ml), washed with water (4×10 ml), 2N NaOH (4×10 ml), water (4×10 ml), dried (Na2SO4) and evaporated to dryness. The residue was purified by flash chromatography eluting with petroleum ether:ethyl acetate 100:2 to give 0.2 g (68%) of the title compound as an ivory solid.

Workup

  1. washwashed with water (4×10 ml), 2N NaOH (4×10 ml), water (4×10 ml)
  2. dry with materialdried (Na2SO4)
  3. customevaporated to dryness
  4. customThe residue was purified by flash chromatography
  5. washeluting with petroleum ether:ethyl acetate 100:2

Sources & evidence

ORD record
ord-65f6121a63104674802964f73642349d
Source dataset
uspto-grants-2001_10
Patent number
US06303606B1

Reaction notes

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