Imidazole → 12-(Boc-amino)-1-dodecyl iodine
Reaction equation
O[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18].N1C=CN=C1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:46]I>C1(C)C=CC=CC=1.C(OCC)(=O)C.O1CCCC1>[I:46][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18]Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
To a suspension of 0.5 g of tert-butyl N-(12-hydroxydodecyl)carbamate in 15 ml of toluene were added 0.28 g of imidazole, 1.09 g of triphenylphosphine and 0.84 g of iodine and the mixture was stirred for 0.5 hour. Then, 5 ml of tetrahydrofuran was further added and the mixture was stirred for 2 hours. To the reaction solution was added ethyl acetate and the mixture was washed successively with a 10% aqueous solution of sodium thiosulfate and water and dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The residue thus obtained was chromatographed over a silica gel column to afford 0.42 g of the title compound.
Workup
- stirringthe mixture was stirred for 2 hours
- washthe mixture was washed successively with a 10% aqueous solution of sodium thiosulfate and water
- dry with materialdried over anhydrous sodium sulfate
- distillationthe solvent was distilled off under reduced pressure
- customThe residue thus obtained
- customwas chromatographed over a silica gel column
Sources & evidence
- ORD record
- ord-de3615deda3c4f6d90a6c9a2ead075d7
- Source dataset
- uspto-grants-2000_04
- Patent number
- US06046201
Reaction notes
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