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Chemical Structure| 114787-83-6 Chemical Structure| 114787-83-6
Chemical Structure| 114787-83-6

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Synonyms: N-Boc-3-(3-methyl-4-nitrobenzyl)-L-histidine methyl ester

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CAS No. :114787-83-6
Formula : C20H26N4O6
M.W : 418.44
SMILES Code : COC(=O)[C@H](Cc1cn(Cc2ccc(c(C)c2)[N+]([O-])=O)cn1)NC(=O)OC(C)(C)C
Synonyms :
N-Boc-3-(3-methyl-4-nitrobenzyl)-L-histidine methyl ester
MDL No. :MFCD03427113

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Application In Synthesis

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 114787-83-6 ]

[ 114787-83-6 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 80866-75-7 ]
  • [ 114787-83-6 ]
  • 2
  • [ 80866-75-7 ]
  • 4-(2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-1H-imidazole-1-carboxylic acid tert-butyl ester [ No CAS ]
  • [ 114787-83-6 ]
YieldReaction ConditionsOperation in experiment
With trifluoromethanesulfonic acid anhydride; N-ethyl-N,N-diisopropylamine; In dichloromethane; Process A, Step (1) Synthesis of 3-(3-methyl-4-nitrophenyl)methyl-N-t-butoxycarbonyl-L-histidine methyl ester (IX-2) Trifluoromethanesulfonic anhydride (10.00 g, 0.0354 mol) and dry methylene chloride (60 ml) were placed into a 500 ml separable flask having its interior atmosphere replaced with well dried nitrogen gas, and cooled to -70 C. Then a solution of <strong>[80866-75-7]3-methyl-4-nitrobenzyl alcohol</strong> (5.34 g, 0.0325 mol) and N,N-diisopropylethylamine (6.2 ml, 0.0356 mol) in dry methylene chloride (40 ml) was added dropwise over a period of 15 minutes, followed by stirring for 30 minutes, after which a solution of N,1-bis-t-butoxycarbonyl-L-histidine methyl ester (XI-2) (10.00 g, 0.0271 mol) in dry methylene chloride (40 ml) was further added dropwise over a period of 20 minutes. Thereafter, the reaction flask was taken out of the cooling bath and the mixture was stirred at room temperature for 6 hours. The reaction mixture during rapid stirring was poured into a 0.2M phosphate buffer solution (about 400 ml) to separate the methylene chloride layer, and the residue was washed with a 0.2M phosphate buffer solution (about 400 ml), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain an orange-colored oily material (12.07 g). This crude oily material was purified by silica gel column chromatography (LiChroprep Si60, 300 g, chloroform/methanol=30/1) to obtain the objective compound (IX-2) (4.45 g; yield: 39.3%) as a light-yellow oily material. There were similarly synthesised the corresponding compounds by using the raw compounds of the formulae (XI) and (X) wherein R1 was H, Et, iPr, nBu, or nHex, and R4, R6, R7, R8, and Y were as shown in Table 1 below.
 

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