Hydrochloric Acid → 2,2,2-Trichloroethyl 2-(3-iodo-4-nitrobenzamido)acetate
Reaktionsgleichung
[ClH:1].C(N(CC)CC)C.[I:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][C:18]=1[N+:19]([O-:21])=[O:20])[C:13](Cl)=[O:14].[N+](C1C=C([N+]([O-])=O)C=CC=1C([NH:29][CH2:30][C:31]([O:33][CH2:34]C1C=CC=CC=1)=[O:32])=O)([O-])=O.[CH2:48]([Cl:50])[Cl:49]>O1CCOCC1>[I:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][C:18]=1[N+:19]([O-:21])=[O:20])[C:13]([NH:29][CH2:30][C:31]([O:33][CH2:34][C:48]([Cl:1])([Cl:50])[Cl:49])=[O:32])=[O:14]Komponenten
Edukt 5
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a stirred solution 2,2,2-trichloroethyl N-Boc glycinate (1.25 g, 4.08 mmol) in DCM (10 mL) was added HCl in dioxane (2N, 10 mL) and stirred at rt for 2 h. Solvents were removed under reduced pressure, and was dissolved in DCM (10 mL) and added triethylamine (1.48 mL, 10.23 mmol) at 0° C. A solution of 3-iodo-4-nitrobenzoyl chloride (prepared from 3-iodo-4-nitrobenzoic acid, 1 g and SOCl2, 10 mL) in DCM (10 mL) was added to the above reaction mixture at 0° C. Then the reaction mixture was stirred at rt for 3 h and worked-up as described in intermediate 1 to obtain the product as a cream color solid (1.28 g, 78%), mp 98-100° C. 1H NMR (400 MHz, CDCl3): δ 8.46 (1H, s), 7.90 (2H, s), 6.67 (1H, br s), 4.86 (2H, s), 4.23 (2H, d, J=5.2 Hz); LC-MS (negative ion mode): m/z 479 (M−H)−.
Aufarbeitung
- customSolvents were removed under reduced pressure
- dissolutionwas dissolved in DCM (10 mL)
- stirringThen the reaction mixture was stirred at rt for 3 h
Quellen und Nachweise
- ORD-Eintrag
- ord-546bc20bc3094281bf2a11829ba33a93
- Quelldatensatz
- uspto-grants-2014_12
- Patentnummer
- US08906344B2
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