(3R,4R)-4-benzyloxy-N-[4-hydroxy-1-(toluene-4-sulfonyl)-azepan-3-yl]-benzamide

Base Information

• Chemical Name: (3R,4R)-4-benzyloxy-N-[4-hydroxy-1-(toluene-4-sulfonyl)-azepan-3-yl]-benzamide
• CAS No.: 189013-33-0
• Molecular Formula: C₂₇H₃₀N₂O₅S
• Molecular Weight: 494.612

Synonyms:(3R,4R)-4-benzyloxy-N-[4-hydroxy-1-(toluene-4-sulfonyl)-azepan-3-yl]-benzamide

Chemical Property of (3R,4R)-4-benzyloxy-N-[4-hydroxy-1-(toluene-4-sulfonyl)-azepan-3-yl]-benzamide

Chemical Property:

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Technology Process of (3R,4R)-4-benzyloxy-N-[4-hydroxy-1-(toluene-4-sulfonyl)-azepan-3-yl]-benzamide

There total 4 articles about (3R,4R)-4-benzyloxy-N-[4-hydroxy-1-(toluene-4-sulfonyl)-azepan-3-yl]-benzamide 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: 82.0%

(4-Benzyloxy-phenyl)-[(1R,7S)-3-(toluene-4-sulfonyl)-3,8-diaza-bicyclo[5.1.0]oct-8-yl]-methanone (189013-31-8) → (3R,4R)-4-benzyloxy-N-[4-hydroxy-1-(toluene-4-sulfonyl)-azepan-3-yl]-benzamide (189013-33-0)

Guidance literature:

With water; toluene-4-sulfonic acid; In tetrahydrofuran; at 20 ℃; for 6h;

DOI:10.1016/S0040-4020(97)00167-1

Reference yield:

4-(benzyloxy)benzoic acid chloride (1486-50-6) + C13H20N2O3S*ClH → (3R,4R)-4-benzyloxy-N-[4-hydroxy-1-(toluene-4-sulfonyl)-azepan-3-yl]-benzamide (189013-33-0)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1002/chem.200701991

Reference yield:

4-(benzyloxy)benzoic acid chloride (1486-50-6) → (3R,4R)-4-benzyloxy-N-[4-hydroxy-1-(toluene-4-sulfonyl)-azepan-3-yl]-benzamide (189013-33-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / triethylamine / CH₂Cl₂ / 0 °C

2: 82 percent / water; p-toluenesulfonic acid / tetrahydrofuran / 6 h / 20 °C

With water; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; dichloromethane; 1: Acylation / 2: Ring cleavage;

DOI:10.1016/S0040-4020(97)00167-1

upstream raw materials:

(4-Benzyloxy-phenyl)-[(1R,7S)-3-(toluene-4-sulfonyl)-3,8-diaza-bicyclo[5.1.0]oct-8-yl]-methanone

4-(benzyloxy)benzoic acid chloride

3-[(4-methylphenyl)sulfonyl]perhydro-azireno[2,3-c]azepine

Downstream raw materials:

3,5-Bis-benzyloxy-4-(2-benzyloxy-6-benzyloxycarbonyl-benzoyl)-benzoic acid (3R,4R)-3-(4-benzyloxy-benzoylamino)-1-(toluene-4-sulfonyl)-azepan-4-yl ester

C₆₅H₆₀N₂O₁₃S

3,5-Bis-benzyloxy-4-(2-benzyloxy-6-benzyloxycarbonyl-benzoyl)-benzoic acid (3R,4R)-3-(4-benzyloxy-benzoylamino)-azepan-4-yl ester

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