[4-(R,S)-(4-benzyloxycarbonylguanidino-phenyl)-4-methyl-2,5-dioxo-imidazolidin-1-yl]acetic acid

Base Information

• Chemical Name: [4-(R,S)-(4-benzyloxycarbonylguanidino-phenyl)-4-methyl-2,5-dioxo-imidazolidin-1-yl]acetic acid
• CAS No.: 169808-28-0
• Molecular Formula: C₂₁H₂₁N₅O₆
• Molecular Weight: 439.428

Synonyms:[4-(R,S)-(4-benzyloxycarbonylguanidino-phenyl)-4-methyl-2,5-dioxo-imidazolidin-1-yl]acetic acid

Chemical Property of [4-(R,S)-(4-benzyloxycarbonylguanidino-phenyl)-4-methyl-2,5-dioxo-imidazolidin-1-yl]acetic acid

Chemical Property:

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Technology Process of [4-(R,S)-(4-benzyloxycarbonylguanidino-phenyl)-4-methyl-2,5-dioxo-imidazolidin-1-yl]acetic acid

There total 6 articles about [4-(R,S)-(4-benzyloxycarbonylguanidino-phenyl)-4-methyl-2,5-dioxo-imidazolidin-1-yl]acetic 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: 31.0%

[4-(R,S)-(4-benzyloxycarbonylguanidino-phenyl)-4-methyl-2,5-dioxo-imidazolidin-1-yl]acetic acid methyl ester (169808-27-9) → [4-(R,S)-(4-benzyloxycarbonylguanidino-phenyl)-4-methyl-2,5-dioxo-imidazolidin-1-yl]acetic acid (169808-28-0)

Guidance literature:

With hydrogenchloride; acetic acid; at 80 ℃; for 1.5h;

DOI:10.1021/jm001068s

Reference yield:

N-benzyloxycarbonyl-S-methyl-isothiourea (25508-19-4) → [4-(R,S)-(4-benzyloxycarbonylguanidino-phenyl)-4-methyl-2,5-dioxo-imidazolidin-1-yl]acetic acid (169808-28-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 58 percent / AcOH / methanol / 12 h

2: 31 percent / aq. HCl; AcOH / 1.5 h / 80 °C

With hydrogenchloride; acetic acid; In methanol;

DOI:10.1021/jm001068s

Reference yield:

(4-nitrophenyl)ethanone (100-19-6) → [4-(R,S)-(4-benzyloxycarbonylguanidino-phenyl)-4-methyl-2,5-dioxo-imidazolidin-1-yl]acetic acid (169808-28-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 75 percent / ethanol; H₂O / 5 h / 50 °C

2.1: NaOMe / methanol / 2 h / Heating

2.2: 81 percent / KI / methanol / 10 h / Heating

3.1: 51 percent / aq. CaCl₂; AcOH; Zn / ethanol / 2 h / Heating

4.1: 58 percent / AcOH / methanol / 12 h

5.1: 31 percent / aq. HCl; AcOH / 1.5 h / 80 °C

With hydrogenchloride; sodium methylate; acetic acid; calcium chloride; zinc; In methanol; ethanol; water;

DOI:10.1021/jm001068s

upstream raw materials:

[4-(R,S)-(4-benzyloxycarbonylguanidino-phenyl)-4-methyl-2,5-dioxo-imidazolidin-1-yl]acetic acid methyl ester

N-benzyloxycarbonyl-S-methyl-isothiourea

(4-nitrophenyl)ethanone

[4-(R,S)-(4-amino-phenyl)-4-methyl-2,5-dioxo-imidazolidin-1-yl]acetic acid methyl ester

Downstream raw materials:

{2-[4-(R,S)-(4-benzyloxycarbonyl-guanidino-phenyl)-4-methyl-2,5-dioxo-imidazolidin-1-yl]acetyl}-Asp(O-t-Bu)-(S)-phenylglycine-O-t-Bu

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