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Cas Database

100008-18-2

100008-18-2

100008-18-2

Identification

  • Product Name:Nα-Boc-L-Prolyl-L-phenylalanyl-L-prolyl-glycine methyl ester

  • CAS Number: 100008-18-2

  • EINECS:

  • Molecular Weight:530.621

  • Molecular Formula:C27H38N4O7

  • HS Code:

  • Mol File:100008-18-2.mol

Synonyms:Nα-Boc-L-Prolyl-L-phenylalanyl-L-prolyl-glycine methyl ester

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      Relevant articles and documentsAll total 4 Articles be found

      SYNTHESIS OF β-CASOMORPHINE-5

      Shvachkin, Yu. P.,Krivtsov, V. F.

      , p. 807 (2007/10/02)

      -

      Optimization of the β-casomorphine-5 synthesis

      Hartrodt,Neubert,Matthies,et al.

      , p. 201 - 201 (2007/10/02)

      -

      Coupling in the absence of a tertiary base: A method for the deprotonation of hydrochloride salts of peptide esters to free amino peptide esters

      Tantry, Subramanyam J.,Ananda,Suresh Babu

      , p. 1028 - 1031 (2007/10/03)

      The deprotonation of hydrochloride salts of peptide esters is accomplished using activated zinc dust. The reaction is neat and quantitative. Addition of a tertiary base is eliminated during the coupling. The free amino peptide esters have been isolated in good yield and purity. This method is extended for the synthesis of β-casomorphin (Tyr-Pro-Phe-Pro-Gly). During its synthesis, all the intermediate free amino peptide esters have been isolated and characterized.

      A rapid and efficient synthesis of β-casomorphin employing Boc-amino acids and 9-fluorenylmethyl chloroformate as a coupling agent

      Babu, V.V. Suresh,Tantry

      , p. 2708 - 2712 (2007/10/03)

      The synthesis of β-casomorphin H-Tyr-Pro-Phe-Pro-Gly-OH employing Boc group for Nα-protection and 9-fluorenylmethyl chloroformate (Fmoc-Cl) for the formation of peptide bond is described. The protocol employing Fmoc-Cl as coupling reagent is found to be simple, efficient and rapid. All the intermediate peptides as well as the final protected peptide Boc-Tyr( iBu)-Pro-Phe-Pro-Gly-OMe have been isolated and fully characterized. They have been obtained in good yield and with high purity.

      Process route upstream and downstream products

      Process route

      1-(tert-butoxycarbonyl)-L-proline
      15761-39-4,59433-50-0

      1-(tert-butoxycarbonyl)-L-proline

      H-Phe-Pro-Gly-OMe
      77434-41-4

      H-Phe-Pro-Gly-OMe

      N<sup>α</sup>-Boc-L-Prolyl-L-phenylalanyl-L-prolyl-glycine methyl ester
      100008-18-2

      Nα-Boc-L-Prolyl-L-phenylalanyl-L-prolyl-glycine methyl ester

      Conditions
      ConditionsYield
      With benzotriazol-1-ol; dicyclohexyl-carbodiimide;Intetrahydrofuran;cooling;
      		80%
      With 4-methyl-morpholine; (fluorenylmethoxy)carbonyl chloride;Intetrahydrofuran;at -15 ℃; for 0.5h;
      		80%
      tert-butyloxycarbonyl-prolyl-glycine methyl ester
      34290-72-7,92132-25-7,1097194-13-2

      tert-butyloxycarbonyl-prolyl-glycine methyl ester

      N<sup>α</sup>-Boc-L-Prolyl-L-phenylalanyl-L-prolyl-glycine methyl ester
      100008-18-2

      Nα-Boc-L-Prolyl-L-phenylalanyl-L-prolyl-glycine methyl ester

      Conditions
      ConditionsYield
      Multi-step reaction with 4 steps
      1.1: HCl / ethyl acetate; H2O / 0.5 h
      1.2: 86 percent / Zn dust / tetrahydrofuran / 0.17 h / 20 °C
      2.1: 87 percent / Fmoc-Cl; NMM / tetrahydrofuran / 0.5 h / -15 °C
      3.1: HCl / ethyl acetate; H2O / 0.5 h
      3.2: 81 percent / Zn dust / tetrahydrofuran / 0.17 h / 20 °C
      4.1: 80 percent / Fmoc-Cl; NMM / tetrahydrofuran / 0.5 h / -15 °C
      With 4-methyl-morpholine; hydrogenchloride; (fluorenylmethoxy)carbonyl chloride;Intetrahydrofuran; water; ethyl acetate;
      Multi-step reaction with 4 steps
      1: 86 percent / HCl / ethyl acetate / 0.5 h
      2: 87 percent / DCC; HOBt / tetrahydrofuran / cooling
      3: 81 percent / HCl / ethyl acetate / 0.5 h
      4: 80 percent / DCC; HOBt / tetrahydrofuran / cooling
      With hydrogenchloride; benzotriazol-1-ol; dicyclohexyl-carbodiimide;Intetrahydrofuran; ethyl acetate;
      Multi-step reaction with 2 steps
      1: activated-ester and mixed anhydride methods
      2: activated-ester and mixed anhydride methods
      Multi-step reaction with 2 steps
      1: 1.) HCl / 1.) AcOH
      2: 1.) HCl / 1.) AcOH
      With hydrogenchloride;
      H-Pro-Gly-OMe
      33256-35-8

      H-Pro-Gly-OMe

      N<sup>α</sup>-Boc-L-Prolyl-L-phenylalanyl-L-prolyl-glycine methyl ester
      100008-18-2

      Nα-Boc-L-Prolyl-L-phenylalanyl-L-prolyl-glycine methyl ester

      Conditions
      ConditionsYield
      Multi-step reaction with 3 steps
      1.1: 87 percent / Fmoc-Cl; NMM / tetrahydrofuran / 0.5 h / -15 °C
      2.1: HCl / ethyl acetate; H2O / 0.5 h
      2.2: 81 percent / Zn dust / tetrahydrofuran / 0.17 h / 20 °C
      3.1: 80 percent / Fmoc-Cl; NMM / tetrahydrofuran / 0.5 h / -15 °C
      With 4-methyl-morpholine; hydrogenchloride; (fluorenylmethoxy)carbonyl chloride;Intetrahydrofuran; water; ethyl acetate;
      Multi-step reaction with 3 steps
      1: 87 percent / DCC; HOBt / tetrahydrofuran / cooling
      2: 81 percent / HCl / ethyl acetate / 0.5 h
      3: 80 percent / DCC; HOBt / tetrahydrofuran / cooling
      With hydrogenchloride; benzotriazol-1-ol; dicyclohexyl-carbodiimide;Intetrahydrofuran; ethyl acetate;
      N<sup>α</sup>-Boc-L-phenylalanyl-L-prolyl-glycine methyl ester
      100008-17-1

      Nα-Boc-L-phenylalanyl-L-prolyl-glycine methyl ester

      N<sup>α</sup>-Boc-L-Prolyl-L-phenylalanyl-L-prolyl-glycine methyl ester
      100008-18-2

      Nα-Boc-L-Prolyl-L-phenylalanyl-L-prolyl-glycine methyl ester

      Conditions
      ConditionsYield
      Multi-step reaction with 2 steps
      1.1: HCl / ethyl acetate; H2O / 0.5 h
      1.2: 81 percent / Zn dust / tetrahydrofuran / 0.17 h / 20 °C
      2.1: 80 percent / Fmoc-Cl; NMM / tetrahydrofuran / 0.5 h / -15 °C
      With 4-methyl-morpholine; hydrogenchloride; (fluorenylmethoxy)carbonyl chloride;Intetrahydrofuran; water; ethyl acetate;
      Multi-step reaction with 2 steps
      1: 81 percent / HCl / ethyl acetate / 0.5 h
      2: 80 percent / DCC; HOBt / tetrahydrofuran / cooling
      With hydrogenchloride; benzotriazol-1-ol; dicyclohexyl-carbodiimide;Intetrahydrofuran; ethyl acetate;
      1-(tert-butoxycarbonyl)-L-proline
      15761-39-4,59433-50-0

      1-(tert-butoxycarbonyl)-L-proline

      N<sup>α</sup>-Boc-L-Prolyl-L-phenylalanyl-L-prolyl-glycine methyl ester
      100008-18-2

      Nα-Boc-L-Prolyl-L-phenylalanyl-L-prolyl-glycine methyl ester

      Conditions
      ConditionsYield
      Multi-step reaction with 5 steps
      1.1: 90 percent / Fmoc-Cl; NMM / tetrahydrofuran / 0.5 h / -15 °C
      2.1: HCl / ethyl acetate; H2O / 0.5 h
      2.2: 86 percent / Zn dust / tetrahydrofuran / 0.17 h / 20 °C
      3.1: 87 percent / Fmoc-Cl; NMM / tetrahydrofuran / 0.5 h / -15 °C
      4.1: HCl / ethyl acetate; H2O / 0.5 h
      4.2: 81 percent / Zn dust / tetrahydrofuran / 0.17 h / 20 °C
      5.1: 80 percent / Fmoc-Cl; NMM / tetrahydrofuran / 0.5 h / -15 °C
      With 4-methyl-morpholine; hydrogenchloride; (fluorenylmethoxy)carbonyl chloride;Intetrahydrofuran; water; ethyl acetate;
      1-(tert-butoxycarbonyl)-L-proline
      15761-39-4,59433-50-0

      1-(tert-butoxycarbonyl)-L-proline

      N<sup>α</sup>-Boc-L-Prolyl-L-phenylalanyl-L-prolyl-glycine methyl ester
      100008-18-2

      Nα-Boc-L-Prolyl-L-phenylalanyl-L-prolyl-glycine methyl ester

      Conditions
      ConditionsYield
      Multi-step reaction with 5 steps
      1: 90 percent / DCC; HOBt / tetrahydrofuran / cooling
      2: 86 percent / HCl / ethyl acetate / 0.5 h
      3: 87 percent / DCC; HOBt / tetrahydrofuran / cooling
      4: 81 percent / HCl / ethyl acetate / 0.5 h
      5: 80 percent / DCC; HOBt / tetrahydrofuran / cooling
      With hydrogenchloride; benzotriazol-1-ol; dicyclohexyl-carbodiimide;Intetrahydrofuran; ethyl acetate;
      1-(tert-butoxycarbonyl)-L-proline
      15761-39-4,59433-50-0

      1-(tert-butoxycarbonyl)-L-proline

      N<sup>α</sup>-Boc-L-Prolyl-L-phenylalanyl-L-prolyl-glycine methyl ester
      100008-18-2

      Nα-Boc-L-Prolyl-L-phenylalanyl-L-prolyl-glycine methyl ester

      Conditions
      ConditionsYield
      Multi-step reaction with 3 steps
      1: activated-ester and mixed anhydride methods
      2: activated-ester and mixed anhydride methods
      3: activated-ester and mixed anhydride methods
      Multi-step reaction with 3 steps
      1: 79 percent
      2: 1.) HCl / 1.) AcOH
      3: 1.) HCl / 1.) AcOH
      With hydrogenchloride;
      1-(tert-butoxycarbonyl)-L-proline
      15761-39-4,59433-50-0

      1-(tert-butoxycarbonyl)-L-proline

      N<sup>α</sup>-Boc-L-phenylalanyl-L-prolyl-glycine methyl ester
      100008-17-1

      Nα-Boc-L-phenylalanyl-L-prolyl-glycine methyl ester

      N<sup>α</sup>-Boc-L-Prolyl-L-phenylalanyl-L-prolyl-glycine methyl ester
      100008-18-2

      Nα-Boc-L-Prolyl-L-phenylalanyl-L-prolyl-glycine methyl ester

      Conditions
      ConditionsYield
      With hydrogenchloride;Yield given. Multistep reaction; 1.) AcOH;
      Multistep reaction; activated-ester and mixed anhydride methods;
      1-(tert-butoxycarbonyl)-L-proline
      15761-39-4,59433-50-0

      1-(tert-butoxycarbonyl)-L-proline

      H-Phe-Pro-Gly-OMe
      77434-41-4

      H-Phe-Pro-Gly-OMe

      N<sup>α</sup>-Boc-L-Prolyl-L-phenylalanyl-L-prolyl-glycine methyl ester
      100008-18-2

      Nα-Boc-L-Prolyl-L-phenylalanyl-L-prolyl-glycine methyl ester

      Conditions
      ConditionsYield
      With benzotriazol-1-ol; dicyclohexyl-carbodiimide;Intetrahydrofuran;cooling;
      		80%
      With 4-methyl-morpholine; (fluorenylmethoxy)carbonyl chloride;Intetrahydrofuran;at -15 ℃; for 0.5h;
      		80%
      tert-butyloxycarbonyl-prolyl-glycine methyl ester
      34290-72-7,92132-25-7,1097194-13-2

      tert-butyloxycarbonyl-prolyl-glycine methyl ester

      N<sup>α</sup>-Boc-L-Prolyl-L-phenylalanyl-L-prolyl-glycine methyl ester
      100008-18-2

      Nα-Boc-L-Prolyl-L-phenylalanyl-L-prolyl-glycine methyl ester

      Conditions
      ConditionsYield
      Multi-step reaction with 4 steps
      1.1: HCl / ethyl acetate; H2O / 0.5 h
      1.2: 86 percent / Zn dust / tetrahydrofuran / 0.17 h / 20 °C
      2.1: 87 percent / Fmoc-Cl; NMM / tetrahydrofuran / 0.5 h / -15 °C
      3.1: HCl / ethyl acetate; H2O / 0.5 h
      3.2: 81 percent / Zn dust / tetrahydrofuran / 0.17 h / 20 °C
      4.1: 80 percent / Fmoc-Cl; NMM / tetrahydrofuran / 0.5 h / -15 °C
      With 4-methyl-morpholine; hydrogenchloride; (fluorenylmethoxy)carbonyl chloride;Intetrahydrofuran; water; ethyl acetate;
      Multi-step reaction with 4 steps
      1: 86 percent / HCl / ethyl acetate / 0.5 h
      2: 87 percent / DCC; HOBt / tetrahydrofuran / cooling
      3: 81 percent / HCl / ethyl acetate / 0.5 h
      4: 80 percent / DCC; HOBt / tetrahydrofuran / cooling
      With hydrogenchloride; benzotriazol-1-ol; dicyclohexyl-carbodiimide;Intetrahydrofuran; ethyl acetate;
      Multi-step reaction with 2 steps
      1: activated-ester and mixed anhydride methods
      2: activated-ester and mixed anhydride methods
      Multi-step reaction with 2 steps
      1: 1.) HCl / 1.) AcOH
      2: 1.) HCl / 1.) AcOH
      With hydrogenchloride;

      100008-18-2 Upstream products

      100008-18-2 Downstream products

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