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Fmoc-NHNH2 (750 mg, 2.95 MMOL) and bis (pentafluorophenyl) carbonate (1221 mg, 3.1 MMOL) were stirred in dry THF (15 mL) at rt for 18 h. The reaction mixture was diluted with water (50 mL) and extracted with EA (x3). The combined organic fractions were washed with 1 M HCI (X1) and brine (X1), dried (MgSO4), and concentrated to give a clear oil, which solidified in vacuo. Off- white solid. Yield : 1.32 g (96percent). Rf = 0.4 (PE: EA 3: 1). This compound was used crude, since it was partially unstable to purification by both recrystallization and silica chromatography
N-[(CH2)5-COO-t-Bu]-N’-Boc-N’-methyl-ethylenediamine[ No CAS ]
[ 939-69-5 ]
N-[(CH2)5COO-t-Bu]-N’-Boc-N’-methyl-ethylenediamine 6-hydroxybenzo[d]thiazole-2-carbonitrilecarbamate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
77%
[00275j Synthesis of N- [(CR2)5 COO-t-Buj -N?-Boc-N?-methyl-ethylene-diamine 6- hydroxybenzo [dj thiazole-2-carbonitrile-carbamate. To the mixture of 2-cyano-6- hydroxybezothiazole (0.366 g, 2.08 mmol) and bis(pentafluorophenyl) carbonate (0.902 g, 2.29 mmol) in 20 ml of dry THF, TEA (580 uL, 4.16 mmol) was added at room temperature under nitrogen. The mixture was stirred for 30 mm minutes, and N-[(CH2)5-COO-t-Bu]-N?-Boc-N?- methyl-ethylenediamine (1.43 g, 4.16 mmol) in 10 mL dry THF was added. The resulting mixture was stirred at room temperature for over 30 minutes. The solvent was removed, and then the product mixture was dissolved in methylene chloride and washed with saturated K2C03 solution 3 times and once with water. The organic layer was dried over Na2SO4, and the solvent was removed. The compound was purified by flash column chromatography using heptane/ethyl acetate as eluent to give the product in a yield of 77 percent (0.875 g).
N-[(PEG)2-COO-t-Bu]-N‘-Boc-N’-methyl-ethylenediamine[ No CAS ]
[ 939-69-5 ]
N-[(PEG)2COO-t-Bu]-N’-Boc-N’-methyl-ethylenediamine 6-hydroxybenzo[d]thiazole-2-carbonitrilecarbamate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
70%
[00243j Synthesis of N- [(PEG)2 COO-t-Buj -N?-Boc-N?-methyl-ethylene-diamine 6- hydroxybenzo [dj thiazole-2-carbonitrile- carbamate. To the mixture of 2-cyano-6- hydroxybezothiazole (0.803 g, 4.56 mmol) and bis(pentafluorophenyl) carbonate (1.98 g, 5.02 mmol) in 40 ml of dry THF, TEA (0.293 g, 2.89 mmol) was added at room temperature under nitrogen. The mixture was stirred for 1 hour, and N-t-butylCOO (PEG)3-N?-BOC-N?-methyl ethylenediamine (3 .56g, 9.12 mmol) in 18 mL dry THF was added. The resulting mixture was stirred at room temperature for over 30 minutes after which the solvent was removed. The product mixture was dissolved in methylene chloride and washed with sat K2C03 solution three times and once with water, then the organic layer was dried over Na2SO4. The compound was purified by flash column chromatography using heptane/ethyl acetate as eluent to give the product in a yield of 70 percent (1.90 g).
N-[(CH2)3-COO-t-Bu]-N’-Boc-N’-methyl-ethylenediamine[ No CAS ]
[ 939-69-5 ]
N-[(CH2)3COO-t-Bu]-N’-Boc-N’-methyl-ethylenediamine 6-hydroxybenzo[d]thiazole-2-carbonitrilecarbamate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
86%
[002591 Synthesis of N- [(CR2)3 COO-t-Buj -N?-Boc-N?-methyl-ethylene-diamine 6- hydroxybenzo [dl thiazole-2-carbonitrile-carbamate. To the mixture of 2-cyano-6- hydroxybezothiazole (0.5 87 g, 3.33 mmol) and bis(pentafluorophenyl) carbonate (1.44 g, 3.66 mmol) in 30 ml of dry THF, TEA (930 iL, 6.66 mmol) was added at room temperature under nitrogen. The mixture was stirred for 30 mm minutes, and N-[(CH2)3-COO-t-Bu]-N?-Boc-N?- methyl-ethylenediamine (2.11 g, 6.66 mmol) in 20 mL dry THF was added. The resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was then dried down, and the product mixture was dissolved in methylene chloride and washed with saturated K2C03 solution 3 times and once with water, then dried over Na2SO4. The solvent was removed, and the compound was purified by flash column chromatography using heptane/ethyl acetate as eluent to give the product in a yield of 86 percent (1.5 g)
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