Trichloroacetic Acid → HCID 1738176, compound

HRID 870025Notes

Reaction equation

HRID 870025 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][O:5][C:6]([C:8]1[O:14][C:13]([CH3:16])([CH3:15])[CH2:12][C:10](=[O:11])[CH:9]=1)=[O:7].ClC(Cl)(Cl)C(O)=O>CCOCC>[CH3:16][C:13]1([CH3:15])[O:14][C@H:8]([C:6]([O:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:7])[CH2:9][C:10](=[O:11])[CH2:12]1

Participants

4

Reactant 2

HCID 6421Trichloroacetic AcidHCID 107602,2-Dimethyl-6-carbobutoxy-2,3-dihydro-4-pyrone

Product 1

HCID 1738176HCID 1738176, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of Indalon (230 mg) and 2R,5R-5-butyl-methyl-2-(5-methylfuran-2-yl) imidazolidin-4-one (55 mg) in dry ether (4.6 mL) was stirred and cooled at ice bath temp (0-4° C.) as t-Butyl Hantzch ester (346 mg) and trichloroacetic acid (32 mg) were added sequentially. The resulted yellow solution was stirred at ice bath temp for 3 days, and monitored by TLC. The reaction mix was passed through a short pad of silica gel and eluted with ether (60 mL). Concentration of the ether and purified by flash chromatography (20% EtOAc in Hexane) gave 204 mg (88%) of the product as oil: 1H NMR (400 MHz, CDCl3) δ 4.46 (dd, 1H, J=4.0, 11.0 Hz), 4.19 (td, 2H, J=2.7, 6.7 Hz), 2.58 (dd, 1H, J=1.6, 14.0 Hz), 2.56 (d, 1H, J=13.2), 2.50 (s, H, J=13.2 Hz), 2.32 (dd, 1H, J=1.6, 14.0 Hz), 1.64 (m, 2H), 1.46 (s, 3H), 1.37 (m, 2H), 1.23 (s, 3H), 0.94 (t, 3H, J=7.4 Hz); 13C NMR (CDCl3, 100 MHz) ä 205.2, 170.1, 76.2, 70.0, 65.4, 52.9, 43.5, 30.5, 28.6, 28.0, 23.8, 19.0, 13.6.

Workup

  1. additionwere added sequentially
  2. additionThe reaction mix
  3. washeluted with ether (60 mL)
  4. customConcentration of the ether and purified by flash chromatography (20% EtOAc in Hexane)

Sources & evidence

ORD record
ord-836820a2047f4c40aa58426202702bd8
Source dataset
uspto-grants-2015_03
Patent number
US08969405B2

Reaction notes

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