Triethylamine → Methyl 2-[2-[4-(8-thia-1,6-diazabicyclo[4.3.0]nonane-7-on-9-ylimino)-3-fluorophenoxymethyl]-5-methylphenoxy]propionate

HRID 482433Notes

Reaction equation

HRID 482433 reaction equation
[N:1]1([C:7]([NH:9][C:10]2[CH:31]=[CH:30][C:13]([O:14][CH2:15][C:16]3[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][C:17]=3[O:18][CH:19]([CH3:24])[C:20]([O:22][CH3:23])=[O:21])=[CH:12][C:11]=2[F:32])=[S:8])[CH2:6][CH2:5][CH2:4][CH2:3][NH:2]1.Cl[C:34](OC(Cl)(Cl)Cl)=[O:35].C(N(CC)CC)C>O1CCOCC1>[N:1]12[CH:7]([N:9]=[C:10]3[CH:31]=[CH:30][C:13]([O:14][CH2:15][C:16]4[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][C:17]=4[O:18][CH:19]([CH3:24])[C:20]([O:22][CH3:23])=[O:21])=[CH:12][CH:11]3[F:32])[S:8][C:34](=[O:35])[N:2]1[CH2:3][CH2:4][CH2:5][CH2:6]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10426DiphosgeneHCID 54069749Methyl 2-[2-[4-(perhydropyridazin-1-ylthiocarbonylamino)-3-fluorophenoxy-methyl]-5-methylphenoxy]propionate

Product 1

HCID 86747368Methyl 2-[2-[4-(8-thia-1,6-diazabicyclo[4.3.0]nonane-7-on-9-ylimino)-3-fluorophenoxymethyl]-5-methylphenoxy]propionateYield 31.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

By the method of Example 1, Step D, of U.S. Pat. No. 4,906,281, 1.50 g (0.00325 mole) of methyl 2-[2-[4-(perhydropyridazin-1-ylthiocarbonylamino)-3-fluorophenoxymethyl]-5-methylphenoxy]propionate and 0.36 g (0.09017 mole) of trichloromethyl chloroformate were reacted in the presence of 0.36 g (0.0035 mole) of triethylamine in 35 mL of dioxane, yielding 0.50 g of methyl 2-[2-[4-(8-thia-1,6-diazabicyclo[4.3.0]nonane-7-on-9-ylimino)-3-fluorophenoxymethyl]-5-methylphenoxy]propionate as a syrup. The NMR and IR spectra were consistent with the proposed structure. NMR: 1.60 (d, 3H, JHH=8.0 Hz); 1.78-1.96 (m, 4H); 2.30 (s, 3H); 3.64-3.80 (m, 4H); 3.70 (s, 3H); 4.80 (q,1H, JHH=8.0 Hz); 5.10 (dd, 2H); 6.58-7.30 (m, 6H).

Sources & evidence

ORD record
ord-13ec94952d904c1099851c4585266066
Source dataset
uspto-grants-1998_08
Patent number
US05798316

Reaction notes

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