Carbamic acid, [(1S,2R)-3-[[(2-amino-6-benzothiazolyl)sulfonyl](2-methylpropyl)amino]- 2-hydroxy-1-(phenylmethyl)propyl]-, 3-pyridinylmethyl ester

Base Information

• Chemical Name: Carbamic acid, [(1S,2R)-3-[[(2-amino-6-benzothiazolyl)sulfonyl](2-methylpropyl)amino]- 2-hydroxy-1-(phenylmethyl)propyl]-, 3-pyridinylmethyl ester
• CAS No.: 656236-15-6
• Molecular Formula: C28H33N5O5S2
• Molecular Weight: 583.733
• Mol file: 656236-15-6.mol

Synonyms:

Chemical Property of Carbamic acid, [(1S,2R)-3-[[(2-amino-6-benzothiazolyl)sulfonyl](2-methylpropyl)amino]- 2-hydroxy-1-(phenylmethyl)propyl]-, 3-pyridinylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Carbamic acid, [(1S,2R)-3-[[(2-amino-6-benzothiazolyl)sulfonyl](2-methylpropyl)amino]- 2-hydroxy-1-(phenylmethyl)propyl]-, 3-pyridinylmethyl ester

There total 7 articles about Carbamic acid, [(1S,2R)-3-[[(2-amino-6-benzothiazolyl)sulfonyl](2-methylpropyl)amino]- 2-hydroxy-1-(phenylmethyl)propyl]-, 3-pyridinylmethyl 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: 68.0%

3-hydroxymethylpyridin (100-55-0) + di(succinimido) carbonate (74124-79-1) + 3-S-amino-2R-hydroxy-1-[(2-aminobenzothiazol-6-sulfonyl)(2-methylpropyl)amino]-4-phenylbutane (183554-21-4) → {(1S,2R)-3-[(2-amino-benzothiazole-6-sulfonyl)-isobutyl-amino]-1-benzyl-2-hydroxypropyl}-carbamic acid pyridin-3-ylmethyl ester (656236-15-6)

Guidance literature:

3-hydroxymethylpyridin; di(succinimido) carbonate; With pyridine; In acetonitrile; for 0.5h;

3-S-amino-2R-hydroxy-1-[(2-aminobenzothiazol-6-sulfonyl)(2-methylpropyl)amino]-4-phenylbutane; In acetonitrile; at 20 ℃; for 16h;

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) → {(1S,2R)-3-[(2-amino-benzothiazole-6-sulfonyl)-isobutyl-amino]-1-benzyl-2-hydroxypropyl}-carbamic acid pyridin-3-ylmethyl ester (656236-15-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 93 percent / CuSO₄ / methanol / 2 h / Heating

2.1: pyridine / acetonitrile / 0.5 h

2.2: 68 percent / acetonitrile / 16 h / 20 °C

With pyridine; copper(II) sulfate; In methanol; acetonitrile;

DOI:10.1016/j.bmc.2003.07.001

Reference yield:

(2R,3S)-3-benzyloxycarbonylamino-2-hydroxy-1-(N-isobutylamino)-4-phenylbutane (143224-62-8) → {(1S,2R)-3-[(2-amino-benzothiazole-6-sulfonyl)-isobutyl-amino]-1-benzyl-2-hydroxypropyl}-carbamic acid pyridin-3-ylmethyl ester (656236-15-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 75 percent / Et₃N / CH₂Cl₂ / 0 - 20 °C

2.1: 70 percent / H₂ / Pd/C / ethyl acetate

3.1: 94 percent / Et₃N / tetrahydrofuran / 16 h

4.1: 93 percent / CuSO₄ / methanol / 2 h / Heating

5.1: pyridine / acetonitrile / 0.5 h

5.2: 68 percent / acetonitrile / 16 h / 20 °C

With pyridine; hydrogen; copper(II) sulfate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; acetonitrile;

DOI:10.1016/j.bmc.2003.07.001

upstream raw materials:

3-hydroxymethylpyridin

di(succinimido) carbonate

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