N-[(benzyloxy)carbonyl]-(S)-phenylalanyl-(R/S)-methyl(ethyl)glycyl-(S)-proline

Base Information

Chemical Name:N-[(benzyloxy)carbonyl]-(S)-phenylalanyl-(R/S)-methyl(ethyl)glycyl-(S)-proline
CAS No.:445396-44-1
Molecular Formula:C₂₇H₃₃N₃O₆
Molecular Weight:495.576
Hs Code.:

Synonyms:N-[(benzyloxy)carbonyl]-(S)-phenylalanyl-(R/S)-methyl(ethyl)glycyl-(S)-proline

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Chemical Property of N-[(benzyloxy)carbonyl]-(S)-phenylalanyl-(R/S)-methyl(ethyl)glycyl-(S)-proline

Chemical Property:

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Technology Process of N-[(benzyloxy)carbonyl]-(S)-phenylalanyl-(R/S)-methyl(ethyl)glycyl-(S)-proline

There total 7 articles about N-[(benzyloxy)carbonyl]-(S)-phenylalanyl-(R/S)-methyl(ethyl)glycyl-(S)-proline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

: 445396-42-9
methyl N-[(benzyloxy)carbonyl]-(S)-phenylalanyl-(R/S)-methyl(ethyl)glycyl-(S)-prolinate

: 445396-44-1
N-[(benzyloxy)carbonyl]-(S)-phenylalanyl-(R/S)-methyl(ethyl)glycyl-(S)-proline

Guidance literature:: With lithium hydroxide; In tetrahydrofuran; methanol; water; for 4h;
DOI:10.1002/1522-2675(200203)85:3<885::AID-HLCA885>3.0.CO;2-Z

Reference yield:

: 2577-48-2
methyl (2S)-pyrrolidine carboxylate

: 445396-44-1
N-[(benzyloxy)carbonyl]-(S)-phenylalanyl-(R/S)-methyl(ethyl)glycyl-(S)-proline

Guidance literature:: Multi-step reaction with 6 steps

1.1: 94 percent / Et₃N / CH₂Cl₂ / 15 h / 20 °C

2.1: 70 percent / Lawesson reagent / toluene / 1.25 h / Heating

3.1: COCl₂; DMF / CH₂Cl₂ / 1 h / 0 - 20 °C

3.2: 1,4-diazabicyclo[2.2.2]octane / tetrahydrofuran / 0.33 h / 20 °C

4.1: NaN₃ / tetrahydrofuran / 20 °C

5.1: 90 percent / acetonitrile / 22 h / 20 °C

6.1: 100 percent / LiOH*H₂O / tetrahydrofuran; methanol; H₂O / 4 h

With Lawessons reagent; lithium hydroxide; sodium azide; triethylamine; N,N-dimethyl-formamide; In tetrahydrofuran; methanol; dichloromethane; water; toluene; acetonitrile;
DOI:10.1002/1522-2675(200203)85:3<885::AID-HLCA885>3.0.CO;2-Z

Reference yield:

: 147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7
L-proline

: 445396-44-1
N-[(benzyloxy)carbonyl]-(S)-phenylalanyl-(R/S)-methyl(ethyl)glycyl-(S)-proline

Guidance literature:: Multi-step reaction with 7 steps

1.1: SOCl₂ / 1 h / Heating

2.1: 94 percent / Et₃N / CH₂Cl₂ / 15 h / 20 °C

3.1: 70 percent / Lawesson reagent / toluene / 1.25 h / Heating

4.1: COCl₂; DMF / CH₂Cl₂ / 1 h / 0 - 20 °C

4.2: 1,4-diazabicyclo[2.2.2]octane / tetrahydrofuran / 0.33 h / 20 °C

5.1: NaN₃ / tetrahydrofuran / 20 °C

6.1: 90 percent / acetonitrile / 22 h / 20 °C

7.1: 100 percent / LiOH*H₂O / tetrahydrofuran; methanol; H₂O / 4 h

With Lawessons reagent; lithium hydroxide; thionyl chloride; sodium azide; triethylamine; N,N-dimethyl-formamide; In tetrahydrofuran; methanol; dichloromethane; water; toluene; acetonitrile;
DOI:10.1002/1522-2675(200203)85:3<885::AID-HLCA885>3.0.CO;2-Z