N-[1-[4-(1-dodecynyl)-2-thienyl]-3-hydroxy-2-propyl]acetamide → 2-Amino-3-[4-(1-dodecynyl)-2-thienyl]-1-propanol
Reaction equation
[C:1]([C:13]1[CH:14]=[C:15]([CH2:18][CH:19]([NH:22]C(=O)C)[CH2:20][OH:21])[S:16][CH:17]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]>C(O)C>[NH2:22][CH:19]([CH2:18][C:15]1[S:16][CH:17]=[C:13]([C:1]#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH:14]=1)[CH2:20][OH:21]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 65 °C
Procedure
To a solution of N-[1-[4-(1-dodecynyl)-2-thienyl]-3-hydroxy-2-propyl]acetamide (4.6 g) in 95% ethanol (30 ml) was added degassed 2N sodium hydroxide solution. The reaction mixture was stirred at 65° C. overnight. The solution was diluted with saturated ammonium chloride solution and extracted with ethyl acetate. The organic extracts were evaporated, and the residue was flashed chromatographed on silica gel (9:1 dichloromethane:methanol). The appropriate fractions were collected and evaporated. The residue was taken up in ether, an ethereal hydrogen chloride was added, and the mixture was stirred at room temperature for 30 mins. The precipitate was collected and air-dried to give 2.05 g (45.4%) of product, mp 85-135° C.
Workup
- customdegassed 2N sodium hydroxide solution
- additionThe solution was diluted with saturated ammonium chloride solution
- extractionextracted with ethyl acetate
- customThe organic extracts were evaporated
- customthe residue was flashed chromatographed on silica gel (9:1 dichloromethane:methanol)
- customThe appropriate fractions were collected
- customevaporated
- additionan ethereal hydrogen chloride was added
- stirringthe mixture was stirred at room temperature for 30 mins
- customThe precipitate was collected
- customair-dried
Sources & evidence
- ORD record
- ord-3588291bead54121bc2ff5ea71892236
- Source dataset
- uspto-grants-2002_12
- Patent number
- US06500849B1
Reaction notes
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