2-{(3R)-3-[(tert-butoxycarbonyl)(methyl)amino]-4-methylpentyl}-1,3-thiazole-4-carboxylic acid

Base Information

• Chemical Name: 2-{(3R)-3-[(tert-butoxycarbonyl)(methyl)amino]-4-methylpentyl}-1,3-thiazole-4-carboxylic acid
• CAS No.: 1053805-76-7
• Molecular Formula: C₁₆H₂₆N₂O₄S
• Molecular Weight: 342.459
• Mol file: 1053805-76-7.mol

Synonyms:2-{(3R)-3-[(tert-butoxycarbonyl)(methyl)amino]-4-methylpentyl}-1,3-thiazole-4-carboxylic acid

Chemical Property of 2-{(3R)-3-[(tert-butoxycarbonyl)(methyl)amino]-4-methylpentyl}-1,3-thiazole-4-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-{(3R)-3-[(tert-butoxycarbonyl)(methyl)amino]-4-methylpentyl}-1,3-thiazole-4-carboxylic acid

There total 1 articles about 2-{(3R)-3-[(tert-butoxycarbonyl)(methyl)amino]-4-methylpentyl}-1,3-thiazole-4-carboxylic acid 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:

ethyl 2-methylthiazole-4-carboxylate (6436-59-5) → 2-{(3R)-3-[(tert-butoxycarbonyl)(methyl)amino]-4-methylpentyl}-1,3-thiazole-4-carboxylic acid (1053805-76-7)

Guidance literature:

Multi-step reaction with 5 steps

1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / Reflux; Inert atmosphere

2: toluene / Reflux; Inert atmosphere

3: potassium tert-butylate / dichloromethane / 20 °C / Inert atmosphere

4: hydrogen; palladium on activated charcoal / methanol / 20 °C

5: water; lithium hydroxide / tetrahydrofuran / 20 °C / Inert atmosphere

With N-Bromosuccinimide; palladium on activated charcoal; potassium tert-butylate; water; hydrogen; lithium hydroxide; dibenzoyl peroxide; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; toluene; 3: |Wittig Olefination;

DOI:10.1111/cbdd.13852

Reference yield: 96.0%

2-{(3R)-3-[(tert-butoxycarbonyl)(methyl)amino]-4-methylpentyl}-1,3-thiazole-4-carboxylic acid (1053805-76-7) + 4-amino-2-methyl-5-phenyl-pent-2-enoic acid ethyl ester → (S,E)-ethyl 4-(2-((R)-3-(tert-butoxycarbonylmethylamino)-4-methylpentyl)thiazole-4-carboxamido)-2-methyl-5-phenylpent-2-enoate

Guidance literature:

With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; Inert atmosphere;

DOI:10.1021/acs.joc.6b01314

Reference yield: 82.0%

(2S,4R)-methyl 4-amino-2-methyl-5-phenylpentanoate hydrochloride + 2-{(3R)-3-[(tert-butoxycarbonyl)(methyl)amino]-4-methylpentyl}-1,3-thiazole-4-carboxylic acid (1053805-76-7) → methyl (2S,4R)-4-{[(2-{(3R)-3-[(tert-butoxycarbonyl)(methyl)amino]-4-methylpentyl}-1,3-thiazol-4-yl)carbonyl]amino}-2-methyl-5-phenylpentanoate

Guidance literature:

2-{(3R)-3-[(tert-butoxycarbonyl)(methyl)amino]-4-methylpentyl}-1,3-thiazole-4-carboxylic acid; With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 0 ℃; for 0.0833333h; Inert atmosphere;

methyl (2S,4R)-4-amino-2-methyl-5-phenylpentanoate hydrochloride; In N,N-dimethyl-formamide; at 0 - 23 ℃; for 24h; Inert atmosphere;

DOI:10.1021/jacs.7b12692

upstream raw materials:

ethyl 2-methylthiazole-4-carboxylate

Downstream raw materials:

methyl (2S,4R)-2-methyl-4-[({2-[(3R)-4-methyl-3-{methyl[(2S,3S)-3-methyl-2-({[(2R)-1-methylpiperidin-2-yl]carbonyl}amino)pentanoyl]amino}pentyl]-1,3-thiazol-4-yl}carbonyl)amino]-5-phenylpentanoate

(2S,4R)-2-methyl-4-[({2-[(3R)-4-methyl-3-{methyl[(2S,3S)-3-methyl-2-({[(2R)-1-methylpiperidin-2-yl]carbonyl}amino)pentanoyl]amino}pentyl]-1,3-thiazol-4-yl}carbonyl)amino]-5-phenylpentanoic acid