methyl (S)-N-({4-[((2S)-2-{[(benzyloxy)carbonyl]amino}-4-methyl-1-oxopentyl)amino]tetrahydro-2H-pyran-4-yl}carbonyl)prolinate

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Chemical Name:methyl (S)-N-({4-[((2S)-2-{[(benzyloxy)carbonyl]amino}-4-methyl-1-oxopentyl)amino]tetrahydro-2H-pyran-4-yl}carbonyl)prolinate
CAS No.:323207-39-2
Molecular Formula:C₂₆H₃₇N₃O₇
Molecular Weight:503.596
Hs Code.:

Synonyms:methyl (S)-N-({4-[((2S)-2-{[(benzyloxy)carbonyl]amino}-4-methyl-1-oxopentyl)amino]tetrahydro-2H-pyran-4-yl}carbonyl)prolinate

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Chemical Property of methyl (S)-N-({4-[((2S)-2-{[(benzyloxy)carbonyl]amino}-4-methyl-1-oxopentyl)amino]tetrahydro-2H-pyran-4-yl}carbonyl)prolinate

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Technology Process of methyl (S)-N-({4-[((2S)-2-{[(benzyloxy)carbonyl]amino}-4-methyl-1-oxopentyl)amino]tetrahydro-2H-pyran-4-yl}carbonyl)prolinate

There total 4 articles about methyl (S)-N-({4-[((2S)-2-{[(benzyloxy)carbonyl]amino}-4-methyl-1-oxopentyl)amino]tetrahydro-2H-pyran-4-yl}carbonyl)prolinate 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:

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

: 323207-39-2
methyl (S)-N-({4-[((2S)-2-{[(benzyloxy)carbonyl]amino}-4-methyl-1-oxopentyl)amino]tetrahydro-2H-pyran-4-yl}carbonyl)prolinate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 89 percent / Et₃N / ethyl acetate / 2 h / 55 °C

2.1: 45 percent / (MeOC₆H₄P(=S)S)2 / toluene / 2 h / Heating

3.1: COCl₂ / CH₂Cl₂; dimethylformamide; toluene / 0.25 h / 20 °C

3.2: DABCO / tetrahydrofuran / 0.67 h / 20 °C

3.3: 74 percent / NaN₃ / tetrahydrofuran / 20 °C

4.1: 73 percent / CH₂Cl₂ / 14 h / 20 °C

With Lawessons reagent; triethylamine; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene;
DOI:10.1002/1522-2675(20001108)83:11<2961::AID-HLCA2961>3.0.CO;2-S

Reference yield:

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

: 323207-39-2
methyl (S)-N-({4-[((2S)-2-{[(benzyloxy)carbonyl]amino}-4-methyl-1-oxopentyl)amino]tetrahydro-2H-pyran-4-yl}carbonyl)prolinate

Guidance literature:: Multi-step reaction with 5 steps

1.1: SOCl₂ / 1 h / Heating

2.1: 89 percent / Et₃N / ethyl acetate / 2 h / 55 °C

3.1: 45 percent / (MeOC₆H₄P(=S)S)2 / toluene / 2 h / Heating

4.1: COCl₂ / CH₂Cl₂; dimethylformamide; toluene / 0.25 h / 20 °C

4.2: DABCO / tetrahydrofuran / 0.67 h / 20 °C

4.3: 74 percent / NaN₃ / tetrahydrofuran / 20 °C

5.1: 73 percent / CH₂Cl₂ / 14 h / 20 °C

With Lawessons reagent; thionyl chloride; triethylamine; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene;
DOI:10.1002/1522-2675(20001108)83:11<2961::AID-HLCA2961>3.0.CO;2-S

Reference yield:

: 323207-17-6
methyl (S)-N-[(tetrahydro-2H-pyran-4-yl)thiocarbonyl]prolinate

: 323207-39-2
methyl (S)-N-({4-[((2S)-2-{[(benzyloxy)carbonyl]amino}-4-methyl-1-oxopentyl)amino]tetrahydro-2H-pyran-4-yl}carbonyl)prolinate

Guidance literature:: Multi-step reaction with 2 steps

1.1: COCl₂ / CH₂Cl₂; dimethylformamide; toluene / 0.25 h / 20 °C

1.2: DABCO / tetrahydrofuran / 0.67 h / 20 °C

1.3: 74 percent / NaN₃ / tetrahydrofuran / 20 °C

2.1: 73 percent / CH₂Cl₂ / 14 h / 20 °C

With COCl₂; In dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1002/1522-2675(20001108)83:11<2961::AID-HLCA2961>3.0.CO;2-S