thiazol-5-ylmethyl ((2R,5R)-5-amino-1,6-diphenylhexan-2-yl)carbamate

Base Information

• Chemical Name: thiazol-5-ylmethyl ((2R,5R)-5-amino-1,6-diphenylhexan-2-yl)carbamate
• CAS No.: 1004316-18-0
• Molecular Formula: C23H27N3O2S
• Molecular Weight: 409.552
• Mol file: 1004316-18-0.mol

Synonyms:thiazol-5-ylmethyl ((2R,5R)-5-amino-1,6-diphenylhexan-2-yl)carbamate;N-[(1R,4R)-4-Amino-5-phenyl-1-(phenylmethyl)pentyl]carbamic acid 5-thiazolylmethyl ester

Chemical Property of thiazol-5-ylmethyl ((2R,5R)-5-amino-1,6-diphenylhexan-2-yl)carbamate

Chemical Property:

• PSA: 105.48000
• LogP: 5.42200

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 5-Thiazolylmethyl N-[(1R,4R)-4-Amino-5-phenyl-1-(phenylmethyl)pentyl]carbamate is an intermediate in the synthesis of 9-(Desmorpholinylethyl) 7,9-(1-Hydroxyethylene) Cobicistat (D296915), an impurity of Cobicistat (O849600), an HIV protease inhibitor and has been coadministered with low-dose ritonavir (R535000) as a pharmacoenhancer, significantly increasing their plasma concentrations.

Technology Process of thiazol-5-ylmethyl ((2R,5R)-5-amino-1,6-diphenylhexan-2-yl)carbamate

There total 10 articles about thiazol-5-ylmethyl ((2R,5R)-5-amino-1,6-diphenylhexan-2-yl)carbamate 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: 92.0%

1,6-diphenyl-5(S)-tert-butoxycarbonylamino-2(S)-(5-thiazolemethoxy)carbonylamino-hexane (1448312-70-6) → C23H27N3O2S (1004316-18-0)

Guidance literature:

With hydrogenchloride; In methanol; dichloromethane; at 20 ℃; Cooling with ice;

Reference yield:

(2R,5R)-1,6-diphenylhexane-2,5-diamine (144186-34-5) + ((5-thiazolyl)methyl)-(4-nitrophenyl)carbonate (144163-97-3) → C23H27N3O2S (1004316-18-0)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In acetonitrile; for 12h;

Reference yield:

methyl (2S)-2-amino-3-phenylpropanoate (2577-90-4) → C23H27N3O2S (1004316-18-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Inert atmosphere

2.1: sodium tetrahydroborate; methanol; lithium chloride / 5 - 20 °C / Inert atmosphere

3.1: triphenylphosphine; N-Bromosuccinimide / N,N-dimethyl-formamide / 0.5 h / 0 - 50 °C / Inert atmosphere

4.1: magnesium; iodine / tetrahydrofuran / 1 h / 20 - 50 °C / Inert atmosphere

4.2: 0.5 h / 0 °C / Inert atmosphere

4.3: 0 - 5 °C / Inert atmosphere

5.1: potassium hydroxide / dimethyl sulfoxide / 0.5 h / 40 - 50 °C

5.2: 1 h / 20 °C

5.3: 3 h

6.1: dibenzoyl peroxide; phosphonic acid diethyl ester / monoethylene glycol diethyl ether / 105 °C

7.1: hydrogenchloride / dichloromethane; methanol / 20 °C / Cooling with ice

With hydrogenchloride; methanol; sodium tetrahydroborate; N-Bromosuccinimide; iodine; magnesium; N-ethyl-N,N-diisopropylamine; phosphonic acid diethyl ester; triphenylphosphine; lithium chloride; potassium hydroxide; dibenzoyl peroxide; In tetrahydrofuran; methanol; dichloromethane; monoethylene glycol diethyl ether; dimethyl sulfoxide; N,N-dimethyl-formamide;

upstream raw materials:

(2R,5R)-1,6-diphenylhexane-2,5-diamine

((5-thiazolyl)methyl)-(4-nitrophenyl)carbonate

1,6-diphenyl-5(S)-tert-butoxycarbonylamino-2(S)-(5-thiazolemethoxy)carbonylamino-hexane

methyl (2S)-2-amino-3-phenylpropanoate

Downstream raw materials:

C₃₉H₅₀N₆O₄S₂

Refernces

• 1、 -. "MODULATORS OF PHARMACOKINETIC PROPERTIES OF THERAPEUTICS". Page/Page column 191-192. . Retrieved 2008/06/13.