Carbon Dioxide → N-[5-(2-Bromoacetamido)pentyl]prop-2-enamide
Reaction equation
FC(F)(F)C([O-])=O.[NH3+:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:15](=[O:18])[CH:16]=[CH2:17].CCN(C(C)C)C(C)C.[Br:28][CH2:29][C:30](Cl)=[O:31].C(=O)=O>C1COCC1.ClCCl.CO.C(O)(C)C>[Br:28][CH2:29][C:30]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:15](=[O:18])[CH:16]=[CH2:17])=[O:31]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
To a suspension of N-(5-ammoniopentyl]acrylamide trifluoracetate (6.12 g, 22.64 mmol) and DIPEA (6.94 ml, 2.2 eq) in THF (120 ml) was added bromoacetyl chloride (2.07 ml, 1.1 eq) through a pressure equalized dropping funnel, over a one hour period and at −60° C. (cardice and isopropanol bath). The reaction mixture was then stirred at room temperature overnight and the completion of the reaction was checked by TLC (dichloromethane:methanol 9:1) the following day. The salts formed during the reaction were filtered off and the reaction mixture evaporated to dryness. The residue was purified by chromatography (neat dichloromethane followed by a gradient of methanol up to 5%). 3.2 g (11.55 mmol, 51%) of the product (N-[5-(2-Bromoacetyl)aminopentyl]acrylamide) were obtained as a white powder. A further recrystallization performed from petroleum ether:ethyl acetate mixture gave 3 g of the product.
Workup
- customat −60° C.
- customThe salts formed during the reaction
- filtrationwere filtered off
- customthe reaction mixture evaporated to dryness
- customThe residue was purified by chromatography (neat dichloromethane
Sources & evidence
- ORD record
- ord-9be62a25616d4988ac2e7061f7a82b34
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08178360B2
Reaction notes
Loading…