methyl N-[(benzyloxy)carbonyl]-(S)-phenylalanyl-dimethylglycyl-(S)-N-methylvalinate

Base Information

Chemical Name:methyl N-[(benzyloxy)carbonyl]-(S)-phenylalanyl-dimethylglycyl-(S)-N-methylvalinate
CAS No.:445396-20-3
Molecular Formula:C₂₈H₃₇N₃O₆
Molecular Weight:511.618
Hs Code.:

Synonyms:methyl N-[(benzyloxy)carbonyl]-(S)-phenylalanyl-dimethylglycyl-(S)-N-methylvalinate

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Chemical Property of methyl N-[(benzyloxy)carbonyl]-(S)-phenylalanyl-dimethylglycyl-(S)-N-methylvalinate

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Technology Process of methyl N-[(benzyloxy)carbonyl]-(S)-phenylalanyl-dimethylglycyl-(S)-N-methylvalinate

There total 6 articles about methyl N-[(benzyloxy)carbonyl]-(S)-phenylalanyl-dimethylglycyl-(S)-N-methylvalinate 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: 83.0%

: 1161-13-3
N-Cbz-L-Phe

: 445396-16-7
methyl (S)-N-(2,2-dimethyl-2H-azirin-3-yl)-N-methylvalinate

: 445396-20-3
methyl N-[(benzyloxy)carbonyl]-(S)-phenylalanyl-dimethylglycyl-(S)-N-methylvalinate

Guidance literature:: In acetonitrile; at 20 ℃; for 19h;
DOI:10.1002/1522-2675(200203)85:3<885::AID-HLCA885>3.0.CO;2-Z

Reference yield:

: 2480-23-1
N-methyl-L-valine

: 445396-20-3
methyl N-[(benzyloxy)carbonyl]-(S)-phenylalanyl-dimethylglycyl-(S)-N-methylvalinate

Guidance literature:: Multi-step reaction with 6 steps

1.1: SOCl₂

2.1: 98 percent / Et₃N / CH₂Cl₂ / 7 h / 40 °C

3.1: 27 percent / Lawesson reagent / tetrahydrofuran / 23 h / 60 °C

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

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

5.1: 46 percent / NaN₃ / tetrahydrofuran / 18 h / 20 °C

6.1: 83 percent / acetonitrile / 19 h / 20 °C

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

Reference yield:

: 3339-44-4
methyl N-methyl-L-valinate hydrochloride

: 445396-20-3
methyl N-[(benzyloxy)carbonyl]-(S)-phenylalanyl-dimethylglycyl-(S)-N-methylvalinate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 98 percent / Et₃N / CH₂Cl₂ / 7 h / 40 °C

2.1: 27 percent / Lawesson reagent / tetrahydrofuran / 23 h / 60 °C

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

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

4.1: 46 percent / NaN₃ / tetrahydrofuran / 18 h / 20 °C

5.1: 83 percent / acetonitrile / 19 h / 20 °C

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