N-[7-bromo-5S-(7-bromo-4S-hydroxy-2,2-dimethyl-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-5S-ylamino)-2,2-dimethyl-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-4S-yl]-4-methyl-benzenesulfonamide

Base Information

• Chemical Name: N-[7-bromo-5S-(7-bromo-4S-hydroxy-2,2-dimethyl-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-5S-ylamino)-2,2-dimethyl-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-4S-yl]-4-methyl-benzenesulfonamide
• CAS No.: 350032-43-8
• Molecular Formula: C₂₅H₃₂Br₂N₂O₇S
• Molecular Weight: 664.412

Synonyms:N-[7-bromo-5S-(7-bromo-4S-hydroxy-2,2-dimethyl-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-5S-ylamino)-2,2-dimethyl-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-4S-yl]-4-methyl-benzenesulfonamide

Chemical Property of N-[7-bromo-5S-(7-bromo-4S-hydroxy-2,2-dimethyl-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-5S-ylamino)-2,2-dimethyl-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-4S-yl]-4-methyl-benzenesulfonamide

Chemical Property:

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Technology Process of N-[7-bromo-5S-(7-bromo-4S-hydroxy-2,2-dimethyl-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-5S-ylamino)-2,2-dimethyl-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-4S-yl]-4-methyl-benzenesulfonamide

There total 4 articles about N-[7-bromo-5S-(7-bromo-4S-hydroxy-2,2-dimethyl-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-5S-ylamino)-2,2-dimethyl-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-4S-yl]-4-methyl-benzenesulfonamide 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: 94.0%

(1S,2S,5R,6R)-3-bromo-5,6-epoxy-1,2-O-isopropylidencyclohex-3-en-1,2-diol (130669-74-8) + (1R,4S,5S,6R)-3-bromo-4,5-(isopropylidenedioxy)-7-(4'-methylphenylsulfonyl)-7-azabicyclo<4.1.0>hept-2-ene (163082-04-0) → N-[7-bromo-5S-(7-bromo-4S-hydroxy-2,2-dimethyl-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-5S-ylamino)-2,2-dimethyl-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-4S-yl]-4-methyl-benzenesulfonamide (350032-43-8)

Guidance literature:

(1R,4S,5S,6R)-3-bromo-4,5-(isopropylidenedioxy)-7-(4'-methylphenylsulfonyl)-7-azabicyclo<4.1.0>hept-2-ene; With ammonia; ytterbium(III) triflate; In dichloromethane; at 50 ℃; for 0.5h;

(1S,2S,5R,6R)-3-bromo-5,6-epoxy-1,2-O-isopropylidencyclohex-3-en-1,2-diol; In 1,4-dioxane; at 60 - 70 ℃; for 3h; Further stages.;

DOI:10.1021/ja0205378

Reference yield: 78.0%

(1R,4S,5S,6R)-3-bromo-4,5-(isopropylidenedioxy)-7-(4'-methylphenylsulfonyl)-7-azabicyclo<4.1.0>hept-2-ene (163082-04-0) → N-[7-bromo-5S-(7-bromo-4S-hydroxy-2,2-dimethyl-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-5S-ylamino)-2,2-dimethyl-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-4S-yl]-4-methyl-benzenesulfonamide (350032-43-8)

Guidance literature:

With ammonia; ytterbium(III) triflate; for 8h; Heating;

Reference yield:

(3aS,7aS)-4-bromo-2,2-dimethyl-3a,7a-dihydro-1,3-benzodioxole (130669-75-9) → N-[7-bromo-5S-(7-bromo-4S-hydroxy-2,2-dimethyl-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-5S-ylamino)-2,2-dimethyl-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-4S-yl]-4-methyl-benzenesulfonamide (350032-43-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: mCPBA / CH₂Cl₂

2.1: NH₃; Yb(OTf)3 / CH₂Cl₂ / 0.5 h / 50 °C

2.2: 94 percent / dioxane / 3 h / 60 - 70 °C

With ammonia; 3-chloro-benzenecarboperoxoic acid; ytterbium(III) triflate; In dichloromethane;

DOI:10.1021/ja0205378

upstream raw materials:

(1R,4S,5S,6R)-3-bromo-4,5-(isopropylidenedioxy)-7-(4'-methylphenylsulfonyl)-7-azabicyclo<4.1.0>hept-2-ene

(1S,2S,5R,6R)-3-bromo-5,6-epoxy-1,2-O-isopropylidencyclohex-3-en-1,2-diol

(3aS,7aS)-4-bromo-2,2-dimethyl-3a,7a-dihydro-1,3-benzodioxole

Downstream raw materials:

acetic acid 7-bromo-5S-[7-bromo-2,2-dimethyl-4S-(toluene-4-sulfonylamino)-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-5S-ylamino]-2,2-dimethyl-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-4S-yl ester

acetic acid 5S-[[2,2-dimethyl-4S-(toluene-4-sulfonylamino)-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-5S-yl]-(2,2,2-trifluoro-acetyl)-amino]-2,2-dimethyl-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-4-yl ester

acetic acid 7-bromo-5S-[[7-bromo-2,2-dimethyl-4S-(toluene-4-sulfonylamino)-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-5S-yl]-(2,2,2-trifluoro-acetyl)-amino]-2,2-dimethyl-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-4S-yl ester

acetic acid 2,2,7-trimethyl-5-[[2,2,7,7-tetramethyl-5S-(toluene-4-sulfonylamino)-hexahydro-benzo[1,2-d;3,4-d']bis[1S,3R]dioxol-4S-yl]-(2,2,2-trifluoro-acetyl)-amino]-hexahydro-benzo[1,2-d;3,4-d']bis[1S,3R]dioxol-4S-yl ester

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