(S)-3-[3-(Adamantan-1-yloxymethyl)-3H-imidazol-4-yl]-2-benzyloxycarbonylamino-propionic acid methyl ester

Base Information

• Chemical Name: (S)-3-[3-(Adamantan-1-yloxymethyl)-3H-imidazol-4-yl]-2-benzyloxycarbonylamino-propionic acid methyl ester
• CAS No.: 177093-72-0
• Molecular Formula: C₂₆H₃₃N₃O₅
• Molecular Weight: 467.565

Synonyms:(S)-3-[3-(Adamantan-1-yloxymethyl)-3H-imidazol-4-yl]-2-benzyloxycarbonylamino-propionic acid methyl ester

Chemical Property of (S)-3-[3-(Adamantan-1-yloxymethyl)-3H-imidazol-4-yl]-2-benzyloxycarbonylamino-propionic acid methyl ester

Chemical Property:

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Technology Process of (S)-3-[3-(Adamantan-1-yloxymethyl)-3H-imidazol-4-yl]-2-benzyloxycarbonylamino-propionic acid methyl ester

There total 7 articles about (S)-3-[3-(Adamantan-1-yloxymethyl)-3H-imidazol-4-yl]-2-benzyloxycarbonylamino-propionic acid methyl ester 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: 83.4%

N(α)-benzyloxycarbonyl-N(τ)-acetyl-L-histidine methyl ester (115374-97-5) + 1-Chloromethoxy-adamantane (177093-80-0) → (S)-3-[3-(Adamantan-1-yloxymethyl)-3H-imidazol-4-yl]-2-benzyloxycarbonylamino-propionic acid methyl ester (177093-72-0)

Guidance literature:

In dichloromethane; for 4h; Ambient temperature;

DOI:10.1039/P19960002139

Reference yield:

1-adamanthanol (768-95-6) → (S)-3-[3-(Adamantan-1-yloxymethyl)-3H-imidazol-4-yl]-2-benzyloxycarbonylamino-propionic acid methyl ester (177093-72-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 80.9 percent / Ac₂O

2: SO₂Cl₂ / CH₂Cl₂

3: 2.) NaHCO₃ / 1.) CH₂Cl₂

With sulfuryl dichloride; acetic anhydride; sodium hydrogencarbonate; In dichloromethane;

DOI:10.1248/cpb.44.871

Reference yield:

1-<(methylthio)methoxy>tricyclo<3.3.1.13,7>decane (133859-39-9) → (S)-3-[3-(Adamantan-1-yloxymethyl)-3H-imidazol-4-yl]-2-benzyloxycarbonylamino-propionic acid methyl ester (177093-72-0)

Guidance literature:

Multi-step reaction with 2 steps

1: SO₂Cl₂ / CH₂Cl₂

2: 2.) NaHCO₃ / 1.) CH₂Cl₂

With sulfuryl dichloride; sodium hydrogencarbonate; In dichloromethane;

DOI:10.1248/cpb.44.871

upstream raw materials:

N(α)-benzyloxycarbonyl-N(τ)-acetyl-L-histidine methyl ester

1-Chloromethoxy-adamantane

1-adamanthanol

1-<(methylthio)methoxy>tricyclo<3.3.1.1^3,7>decane

Downstream raw materials:

L-pyroglutamyl-L-histidyl-L-proline amide

[(S)-1-[3-(Adamantan-1-yloxymethyl)-3H-imidazol-4-ylmethyl]-2-((S)-2-carbamoyl-pyrrolidin-1-yl)-2-oxo-ethyl]-carbamic acid benzyl ester

(S)-3-[3-(Adamantan-1-yloxymethyl)-3H-imidazol-4-yl]-2-benzyloxycarbonylamino-propionic acid

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