methyl (RS)-4-[((S)-2-{[(benzyloxy)carbonyl]amino}-3-methyl-1-oxobutyl)amino]-4-methyl-5-[methyl(phenyl)amino]-5-oxopentanoate

Base Information

• Chemical Name: methyl (RS)-4-[((S)-2-{[(benzyloxy)carbonyl]amino}-3-methyl-1-oxobutyl)amino]-4-methyl-5-[methyl(phenyl)amino]-5-oxopentanoate
• CAS No.: 820244-35-7
• Molecular Formula: C₂₇H₃₅N₃O₆
• Molecular Weight: 497.591
• Mol file: 820244-35-7.mol

Synonyms:methyl (RS)-4-[((S)-2-{[(benzyloxy)carbonyl]amino}-3-methyl-1-oxobutyl)amino]-4-methyl-5-[methyl(phenyl)amino]-5-oxopentanoate

Chemical Property of methyl (RS)-4-[((S)-2-{[(benzyloxy)carbonyl]amino}-3-methyl-1-oxobutyl)amino]-4-methyl-5-[methyl(phenyl)amino]-5-oxopentanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (RS)-4-[((S)-2-{[(benzyloxy)carbonyl]amino}-3-methyl-1-oxobutyl)amino]-4-methyl-5-[methyl(phenyl)amino]-5-oxopentanoate

There total 7 articles about methyl (RS)-4-[((S)-2-{[(benzyloxy)carbonyl]amino}-3-methyl-1-oxobutyl)amino]-4-methyl-5-[methyl(phenyl)amino]-5-oxopentanoate 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: 96.0%

(S)-N-(benzyloxycarbonyl)valine (1149-26-4) + methyl 3-(3-amino-2,N-dimethyl-N-phenyl-2H-azirin-2-yl)propanoate (820244-21-1) → methyl (RS)-4-[((S)-2-{[(benzyloxy)carbonyl]amino}-3-methyl-1-oxobutyl)amino]-4-methyl-5-[methyl(phenyl)amino]-5-oxopentanoate (820244-35-7)

Guidance literature:

In dichloromethane; at 20 ℃; for 24h;

DOI:10.1002/hlca.200490226

Reference yield:

3,4,5,6-tetrahydro-2H-pyran-2-one (542-28-9,26354-94-9) → methyl (RS)-4-[((S)-2-{[(benzyloxy)carbonyl]amino}-3-methyl-1-oxobutyl)amino]-4-methyl-5-[methyl(phenyl)amino]-5-oxopentanoate (820244-35-7)

Guidance literature:

Multi-step reaction with 7 steps

1.1: LDA / tetrahydrofuran / 1 h / -65 - -60 °C

1.2: 44 percent / 1,3-dimethylimidazolidin-2-one / tetrahydrofuran / 4 h / -65 °C

2.1: 88 percent / AlCl₃ / 1,2-dichloro-ethane / 5 h / 15 - 25 °C

3.1: 73 percent / NaIO₄; RuCl₃*H₂O / acetonitrile; ethyl acetate; H₂O / 4 h / 20 °C

4.1: 100 percent / tetrahydrofuran; diethyl ether / 0 - 20 °C

5.1: 93 percent / Lawesson reagent / toluene / 0.5 h / 130 °C

6.1: COCl₂ / toluene; dimethylformamide; CH₂Cl₂ / 0 °C

6.2: DABCO / tetrahydrofuran / 0.42 h / 20 °C

6.3: 90 percent / NaN₃ / dimethylformamide / 72 h / 20 °C

7.1: 96 percent / CH₂Cl₂ / 24 h / 20 °C

With Lawessons reagent; ruthenium trichloride; sodium periodate; aluminium trichloride; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; water; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1002/hlca.200490226

Reference yield:

α-methyl-δ-valerolactone (73746-79-9,80698-15-3,107242-87-5,10603-03-9,823-22-3) → methyl (RS)-4-[((S)-2-{[(benzyloxy)carbonyl]amino}-3-methyl-1-oxobutyl)amino]-4-methyl-5-[methyl(phenyl)amino]-5-oxopentanoate (820244-35-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 88 percent / AlCl₃ / 1,2-dichloro-ethane / 5 h / 15 - 25 °C

2.1: 73 percent / NaIO₄; RuCl₃*H₂O / acetonitrile; ethyl acetate; H₂O / 4 h / 20 °C

3.1: 100 percent / tetrahydrofuran; diethyl ether / 0 - 20 °C

4.1: 93 percent / Lawesson reagent / toluene / 0.5 h / 130 °C

5.1: COCl₂ / toluene; dimethylformamide; CH₂Cl₂ / 0 °C

5.2: DABCO / tetrahydrofuran / 0.42 h / 20 °C

5.3: 90 percent / NaN₃ / dimethylformamide / 72 h / 20 °C

6.1: 96 percent / CH₂Cl₂ / 24 h / 20 °C

With Lawessons reagent; ruthenium trichloride; sodium periodate; aluminium trichloride; In tetrahydrofuran; diethyl ether; dichloromethane; water; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1002/hlca.200490226

upstream raw materials:

(S)-N-(benzyloxycarbonyl)valine

methyl 3-(3-amino-2,N-dimethyl-N-phenyl-2H-azirin-2-yl)propanoate

3,4,5,6-tetrahydro-2H-pyran-2-one

α-methyl-δ-valerolactone

Downstream raw materials:

methyl 3-[(RS)-2-((S)-1-{[(benzyloxy)carbonyl]amino}-2-methylpropyl)-4-methyl-5-oxo-1,3-oxazol-4-yl]propanoate