N-{(1S,2R)-3-[(2-amino-benzothiazole-6-sulfonyl)-isobutyl-amino]-1-benzyl-2-hydroxypropyl}-2-(2,6-dimethyl-phenoxy)-acetamide

Base Information

• Chemical Name: N-{(1S,2R)-3-[(2-amino-benzothiazole-6-sulfonyl)-isobutyl-amino]-1-benzyl-2-hydroxypropyl}-2-(2,6-dimethyl-phenoxy)-acetamide
• CAS No.: 656236-05-4
• Molecular Formula: C₃₁H₃₈N₄O₅S₂
• Molecular Weight: 610.799
• Mol file: 656236-05-4.mol

Synonyms:N-{(1S,2R)-3-[(2-amino-benzothiazole-6-sulfonyl)-isobutyl-amino]-1-benzyl-2-hydroxypropyl}-2-(2,6-dimethyl-phenoxy)-acetamide

Chemical Property of N-{(1S,2R)-3-[(2-amino-benzothiazole-6-sulfonyl)-isobutyl-amino]-1-benzyl-2-hydroxypropyl}-2-(2,6-dimethyl-phenoxy)-acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-{(1S,2R)-3-[(2-amino-benzothiazole-6-sulfonyl)-isobutyl-amino]-1-benzyl-2-hydroxypropyl}-2-(2,6-dimethyl-phenoxy)-acetamide

There total 6 articles about N-{(1S,2R)-3-[(2-amino-benzothiazole-6-sulfonyl)-isobutyl-amino]-1-benzyl-2-hydroxypropyl}-2-(2,6-dimethyl-phenoxy)-acetamide 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: 38.0%

2-(2,6-dimethylphenoxy)acetic acid (13335-71-2) + 3-S-amino-2R-hydroxy-1-[(2-aminobenzothiazol-6-sulfonyl)(2-methylpropyl)amino]-4-phenylbutane (183554-21-4) → N-{(1S,2R)-3-[(2-amino-benzothiazole-6-sulfonyl)-isobutyl-amino]-1-benzyl-2-hydroxypropyl}-2-(2,6-dimethyl-phenoxy)-acetamide (656236-05-4)

Guidance literature:

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In N,N-dimethyl-formamide; at 20 ℃; for 18h;

DOI:10.1016/j.bmc.2003.07.001

Reference yield:

3-S-(N-tert-butyloxyformamido)-[2R-hydroxy-1-[(4-aminophenylsulfonyl)(2-methylpropyl)]amino]-4-phenylbutane (183004-94-6) → N-{(1S,2R)-3-[(2-amino-benzothiazole-6-sulfonyl)-isobutyl-amino]-1-benzyl-2-hydroxypropyl}-2-(2,6-dimethyl-phenoxy)-acetamide (656236-05-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / CuSO₄ / methanol / 2 h / Heating

2: 38 percent / HOBt; EDC / dimethylformamide / 18 h / 20 °C

With benzotriazol-1-ol; copper(II) sulfate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In methanol; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2003.07.001

Reference yield:

(2R,3S)-3-benzyloxycarbonylamino-2-hydroxy-1-(N-isobutylamino)-4-phenylbutane (143224-62-8) → N-{(1S,2R)-3-[(2-amino-benzothiazole-6-sulfonyl)-isobutyl-amino]-1-benzyl-2-hydroxypropyl}-2-(2,6-dimethyl-phenoxy)-acetamide (656236-05-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 75 percent / Et₃N / CH₂Cl₂ / 0 - 20 °C

2: 70 percent / H₂ / Pd/C / ethyl acetate

3: 94 percent / Et₃N / tetrahydrofuran / 16 h

4: 93 percent / CuSO₄ / methanol / 2 h / Heating

5: 38 percent / HOBt; EDC / dimethylformamide / 18 h / 20 °C

With hydrogen; benzotriazol-1-ol; copper(II) sulfate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2003.07.001

upstream raw materials:

2-(2,6-dimethylphenoxy)acetic acid

3-S-amino-2R-hydroxy-1-[(2-aminobenzothiazol-6-sulfonyl)(2-methylpropyl)amino]-4-phenylbutane

(2R,3S)-3-benzyloxycarbonylamino-2-hydroxy-1-(N-isobutylamino)-4-phenylbutane

4-Nitrobenzenesulfonyl chloride