methanesulfonic acid 2-benzyloxycarbonylamino-3-(1-methyl-1H-imidazol-4-yl)-propyl ester

Base Information

• Chemical Name: methanesulfonic acid 2-benzyloxycarbonylamino-3-(1-methyl-1H-imidazol-4-yl)-propyl ester
• CAS No.: 945723-73-9
• Molecular Formula: C₁₆H₂₁N₃O₅S
• Molecular Weight: 367.426

Synonyms:methanesulfonic acid 2-benzyloxycarbonylamino-3-(1-methyl-1H-imidazol-4-yl)-propyl ester

Chemical Property of methanesulfonic acid 2-benzyloxycarbonylamino-3-(1-methyl-1H-imidazol-4-yl)-propyl ester

Chemical Property:

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Technology Process of methanesulfonic acid 2-benzyloxycarbonylamino-3-(1-methyl-1H-imidazol-4-yl)-propyl ester

There total 8 articles about methanesulfonic acid 2-benzyloxycarbonylamino-3-(1-methyl-1H-imidazol-4-yl)-propyl 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: 84.0%

3-[1-(methyl)imidazol-4-yl]-(2S)-2-(benzyloxycarbonylamino)propanol (945723-57-9) + methanesulfonyl chloride (124-63-0) → methanesulfonic acid 2-benzyloxycarbonylamino-3-(1-methyl-1H-imidazol-4-yl)-propyl ester (945723-73-9)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1016/j.tetlet.2006.03.049

Reference yield:

(S)-methyl 2-(benzyloxycarbonylamino)-3-(1-methyl-1H-imidazol-4-yl)propanoate (890306-83-9) → methanesulfonic acid 2-benzyloxycarbonylamino-3-(1-methyl-1H-imidazol-4-yl)-propyl ester (945723-73-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / NaBH₄ / methanol / 3 h / 0 °C

2: triethylamine / CH₂Cl₂ / 3 h / 20 °C

With sodium tetrahydroborate; triethylamine; In methanol; dichloromethane;

DOI:10.1002/chem.200601420

Reference yield:

(R)-7-Methoxycarbonyl-2-methyl-5-oxo-6,7,8,8a-tetrahydro-5H-4λ5-imidazo[1,5-c]pyrimidin-2-ium; iodide → methanesulfonic acid 2-benzyloxycarbonylamino-3-(1-methyl-1H-imidazol-4-yl)-propyl ester (945723-73-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 79 percent / (i-Pr)2NEt / acetonitrile / 48 h / Heating

2: NaBH₄ / methanol / 3 h / 0 °C

3: 84 percent / Et₃N / CH₂Cl₂ / 3 h / 20 °C

With sodium tetrahydroborate; triethylamine; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; acetonitrile;

DOI:10.1016/j.tetlet.2006.03.049

upstream raw materials:

3-[1-(methyl)imidazol-4-yl]-(2S)-2-(benzyloxycarbonylamino)propanol

methanesulfonyl chloride

(S)-methyl 2-(benzyloxycarbonylamino)-3-(1-methyl-1H-imidazol-4-yl)propanoate

S-(+)-7-Methoxycarbonyl-5,6,7,8-tetrahydroimidazo<1,5-c>pyrimidin-5-on

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