acetic acid 5-hydroxy-1-(toluene-4-sulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-4-yl ester

Base Information

• Chemical Name: acetic acid 5-hydroxy-1-(toluene-4-sulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-4-yl ester
• CAS No.: 193686-95-2
• Molecular Formula: C₁₉H₂₁NO₅S
• Molecular Weight: 375.445
• Mol file: 193686-95-2.mol

Synonyms:acetic acid 5-hydroxy-1-(toluene-4-sulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-4-yl ester

Chemical Property of acetic acid 5-hydroxy-1-(toluene-4-sulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of acetic acid 5-hydroxy-1-(toluene-4-sulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-4-yl ester

There total 4 articles about acetic acid 5-hydroxy-1-(toluene-4-sulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-4-yl 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: 40.0%

vinyl acetate (108-05-4,9003-20-7) + cis-4,5-dihydroxy-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine → (4R,5S)-4,5-dihydroxy-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine (193686-96-3) + (4S,5R)-4,5-dihydroxy-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine (193686-94-1) + acetic acid 5-hydroxy-1-(toluene-4-sulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-4-yl ester (193686-95-2)

Guidance literature:

With Lipase QL; at 20 ℃; for 6h;

DOI:10.1016/S0040-4020(00)00388-4

Reference yield:

vinyl acetate (108-05-4,9003-20-7) + 1-(p-toluenesulfonyl)-2,3-dihydro-1H-1-benzazepine (19673-34-8) → (4R,5S)-4,5-dihydroxy-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine (193686-96-3) + (4S,5R)-4,5-dihydroxy-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine (193686-94-1) + acetic acid 5-hydroxy-1-(toluene-4-sulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-4-yl ester (193686-95-2)

Guidance literature:

1-(p-toluenesulfonyl)-2,3-dihydro-1H-1-benzazepine; With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In water; acetone; tert-butyl alcohol; at 20 ℃;

vinyl acetate; With Lipase QL; at 20 ℃;

DOI:10.1016/S0040-4020(00)00388-4

Reference yield:

5-hydroxy-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine (19673-33-7) → acetic acid 5-hydroxy-1-(toluene-4-sulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-4-yl ester (193686-95-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 93 percent / p-toluenesulfonic acid / toluene / 6 h / Heating

2: 69 percent / osmium tetroxide; 4-methylmorpholine N-oxide / acetone; 2-methyl-propan-2-ol; H₂O / 20 °C

3: 40 percent / lipase QL / 6 h / 20 °C

With osmium(VIII) oxide; Lipase QL; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; In water; acetone; toluene; tert-butyl alcohol; 1: Dehydration / 2: Oxidation / 3: Acetylation;

DOI:10.1016/S0040-4020(00)00388-4

upstream raw materials:

vinyl acetate

1-(p-toluenesulfonyl)-2,3-dihydro-1H-1-benzazepine

5-hydroxy-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine

Downstream raw materials:

(4R,5S)-4,5-dihydroxy-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine

(4R,5S)-4,5-dimethylmethylenedioxy-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine