2-(N-benzyloxycarbonyl-N-methylamino)-3-(3-carbamoylguanidino)propionic acid

Base Information

• Chemical Name: 2-(N-benzyloxycarbonyl-N-methylamino)-3-(3-carbamoylguanidino)propionic acid
• CAS No.: 207570-26-1
• Molecular Formula: C₁₄H₁₉N₅O₅
• Molecular Weight: 337.335

Synonyms:2-(N-benzyloxycarbonyl-N-methylamino)-3-(3-carbamoylguanidino)propionic acid

Chemical Property of 2-(N-benzyloxycarbonyl-N-methylamino)-3-(3-carbamoylguanidino)propionic acid

Chemical Property:

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Technology Process of 2-(N-benzyloxycarbonyl-N-methylamino)-3-(3-carbamoylguanidino)propionic acid

There total 3 articles about 2-(N-benzyloxycarbonyl-N-methylamino)-3-(3-carbamoylguanidino)propionic acid 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: 71.0%

2-methyl-2-thiopseudobiuret hydroiodide (34277-75-3) + 3-amino-2-(N-benzyloxycarbonyl-N-methyl)aminopropionic acid (198416-00-1) → 2-(N-benzyloxycarbonyl-N-methylamino)-3-(3-carbamoylguanidino)propionic acid (207570-26-1)

Guidance literature:

With sodium hydroxide; In water; at 20 ℃; for 19h;

DOI:10.1002/(SICI)1099-0690(199805)1998:5<777::AID-EJOC777>3.0.CO;2-W

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → 2-(N-benzyloxycarbonyl-N-methylamino)-3-(3-carbamoylguanidino)propionic acid (207570-26-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 88 percent / NaHCO₃, NaOH / H₂O / 3 h / 20 °C

2: 74 percent / iodobenzene bis(trifluoroacetate), pyridine / H₂O; dimethylformamide / 5 h

3: 71 percent / NaOH / H₂O / 19 h / 20 °C

With pyridine; sodium hydroxide; sodium hydrogencarbonate; bis-[(trifluoroacetoxy)iodo]benzene; In water; N,N-dimethyl-formamide;

DOI:10.1002/(SICI)1099-0690(199805)1998:5<777::AID-EJOC777>3.0.CO;2-W

Reference yield:

N2-benzyloxycarbonyl-N2-methylasparagine (207570-23-8) → 2-(N-benzyloxycarbonyl-N-methylamino)-3-(3-carbamoylguanidino)propionic acid (207570-26-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / iodobenzene bis(trifluoroacetate), pyridine / H₂O; dimethylformamide / 5 h

2: 71 percent / NaOH / H₂O / 19 h / 20 °C

With pyridine; sodium hydroxide; bis-[(trifluoroacetoxy)iodo]benzene; In water; N,N-dimethyl-formamide;

DOI:10.1002/(SICI)1099-0690(199805)1998:5<777::AID-EJOC777>3.0.CO;2-W

upstream raw materials:

2-methyl-2-thiopseudobiuret hydroiodide

3-amino-2-(N-benzyloxycarbonyl-N-methyl)aminopropionic acid

benzyl chloroformate

N²-benzyloxycarbonyl-N²-methylasparagine

Downstream raw materials:

5-(N-benzyloxycarbonyl-N-methylamino)-3,4,5,6-tetrahydro-2-ureidopyrimidin-4-one

5-[N-methyl-N-(N^β,N^ε,N^ω-tri(benzyloxycarbonyl)-(S)-β-homoarginyl)amino]-3,4,5,6-tetrahydro-2-ureidopyrimidin-4-one

TAN1057

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