Triethylamine → HCID 69655535, compound

HRID 2181138Notes

Reaction equation

HRID 2181138 reaction equation
[CH3:1][C:2]1([CH3:12])[O:6][C:5](=[CH:7][C:8]([OH:10])=O)[C:4](=[O:11])[O:3]1.[Cl:13][C:14]1[CH:31]=[CH:30][C:17]([CH2:18][CH:19]([NH:28][CH3:29])[CH2:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)=[CH:16][CH:15]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1.C(N(CC)CC)C>C(#N)C.C(OCC)(=O)C>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([CH2:18][CH:19]([N:28]([CH3:29])[C:8](=[O:10])[CH:7]=[C:5]2[C:4](=[O:11])[O:3][C:2]([CH3:1])([CH3:12])[O:6]2)[CH2:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)=[CH:30][CH:31]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 2724699PyBOPHCID 22485633HCID 22485633, compoundHCID 68860642(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-acetic acid

Product 1

HCID 69655535HCID 69655535, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-acetic acid (0.936 g, 5.43 mmol) in dry acetonitrile (10 ml) was treated successively with [1-(4-chlorobenzyl)-2-(4-chlorophenyl)-ethyl]-methylamine (1.60 g, 5.43 mmol), benzotriazole-1-yl-oxy-tris-pyrrolidino-phosphonium hexafluorophosphate (PyBOP®) (3.11 g, 5.98 mmol) and triethylamine (0.83 ml, 5.98 mmol). After 3 h at 22° C., the clear solution was diluted with ethyl acetate, washed with 0.1 N hydrochloric acid, saturated sodium bicarbonate, brine and dried (magnesium sulfate). Evaporation of the solvent and chromatography of the residue on silica gel (elution toluene-ethyl acetate, 7:3) gave 2.35 g (97% yield) of the title amide as white needles; mp 109° C. (ethyl acetate-hexane). 1HNMR 400 MHz (CDCl3) δ (ppm): mixture of rotamers; 1.62 and 1.69 (6H, 2 s, CH3), 2.75 and 2.97 (3H, 2 s, NCH3), 2.8-2.9 (4H, m, CH2), 4.15 (1H, m, CH), 5.44 and 5.89 (1H, 2 s, CH), 7.05-7.3 (8H, m, aromatics). Anal. calcd for C23H23C12NO4: C, 61.62; H, 5.17; N, 3.12. Found: C, 61.39; H, 5.25; N, 3.22.

Workup

  1. washwashed with 0.1 N hydrochloric acid, saturated sodium bicarbonate, brine
  2. dry with materialdried (magnesium sulfate)
  3. customEvaporation of the solvent and chromatography of the residue on silica gel (elution toluene-ethyl acetate, 7:3)

Sources & evidence

ORD record
ord-1db511e542704704ac9d82f1907ce931
Source dataset
uspto-grants-2005_05
Patent number
US06890942B2

Reaction notes

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