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Chemical Structure| 5211-23-4 Chemical Structure| 5211-23-4
Chemical Structure| 5211-23-4

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Synonyms: Methyl(S)-N-(benzyloxycarbonyl)prolinate; N-Z-L-proline methyl ester

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Product Details of Cbz-Pro-OMe

CAS No. :5211-23-4
Formula : C14H17NO4
M.W : 263.29
SMILES Code : O=C(N1[C@H](C(OC)=O)CCC1)OCC2=CC=CC=C2
Synonyms :
Methyl(S)-N-(benzyloxycarbonyl)prolinate; N-Z-L-proline methyl ester
MDL No. :MFCD00134246
InChI Key :BLQYEDXWEDWCNJ-LBPRGKRZSA-N
Pubchem ID :688168

Safety of Cbz-Pro-OMe

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319
Precautionary Statements:P305+P351+P338

Application In Synthesis of Cbz-Pro-OMe

* 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 [ 5211-23-4 ]

[ 5211-23-4 ] Synthesis Path-Downstream   1~4

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  • 4
  • [ 186581-53-3 ]
  • [ 6216-63-3 ]
  • [ 5211-23-4 ]
YieldReaction ConditionsOperation in experiment
94% NaClO2 (498 mg, 5.507 mmol) was added to a mixed solution containing 150 mg (1.101 mmol) of 3-phenylpropanol in a CH2Cl2 (3.7 mL)-NaH2PO4 aqueous solution (2.1 mL, 0.52 M solution being 1.0 equivalent), followed by stirring. Then, Me-AZADO+Cl- (11.1 mg, 0.05507 mmol) was immediately added, followed by vigorous stirring at room temperature until disappearance of the starting material 3-phenylpropanol and its aldehyde product 3-phenylpropanal was confirmed. After completion of the reaction, 2-methyl-2-butene (1.17 mL, 11.01 mmol) was added under cooling with ice, and an aqueous layer and an organic layer were separated under a weakly acidic condition. To the organic layer, a 10percent sodium hydroxide aqueous solution was added to obtain a solution having a pH 11, from which organic substances other than the ionic carboxylic acid were extracted with diethyl ether. The remained aqueous layer was adjusted to pH 3 with 10percent hydrochloric acid, and from the aqueous layer, a molecular type carboxylic acid was extracted with diethyl ether. The organic layer was washed with an aqueous sodium chloride solution and then dried over magnesium sulfate, and the solvent was distilled off under reduced pressure.The residue was dissolved in methylene chloride, and diazomethane was added under cooling with ice, and after confirming the completion of a methyl esterification reaction, stirring was continued at room temperature for a while. Then, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 176 mg (yield: 97percent) of a methyl ester.Cases wherein the reaction was carried out in the same manner, are shown with respect to the case where Me-AZADO+Cl- was employed and the case where TEMPO+CL- was employed. Here, in the Table, "alcohol" represents the alcohol, "time (hr)" represents the reaction time (unit: hr), "yield (percent)" represents the yield (percent) which was calculated by the isolated yield of the methyl ester by the diazomethane. "note" represents a note, "trace" represents a trace amount, "Additive" represents an additive, "SASS" represents sodium stearate, and "slight chlorination" means that slight chlorination was observed. "Cat." represents the catalyst. TABLE 1 yield percent No. alcohol time [hr] note 1 1.5 77 97 2 1.5 63 93 3 10 trace 84 4 32 trace 86 5 5.5/6.5 trace 99/96Additive (5 mol percent) PhCO2II/ SASS* 6 4.5 20 91 7 10 25 90 8 24 <16 <84 slight chlorination 9 3 <13 <92 slight chlorination cat. 20 mol percent 10 5 - 92 11 1 - 88 12 15 trace 94 SASS*: Stearic Acid Sodium Salt
 

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