(S)-1-[(S)-3-(3-Benzyloxy-phenyl)-2-((S)-2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-propionyl]-hexahydro-pyridazine-3-carboxylic acid methyl ester

Base Information

• Chemical Name: (S)-1-[(S)-3-(3-Benzyloxy-phenyl)-2-((S)-2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-propionyl]-hexahydro-pyridazine-3-carboxylic acid methyl ester
• CAS No.: 222556-14-1
• Molecular Formula: C₃₂H₄₄N₄O₇
• Molecular Weight: 596.724
• Mol file: 222556-14-1.mol

Synonyms:(S)-1-[(S)-3-(3-Benzyloxy-phenyl)-2-((S)-2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-propionyl]-hexahydro-pyridazine-3-carboxylic acid methyl ester

Chemical Property of (S)-1-[(S)-3-(3-Benzyloxy-phenyl)-2-((S)-2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-propionyl]-hexahydro-pyridazine-3-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1-[(S)-3-(3-Benzyloxy-phenyl)-2-((S)-2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-propionyl]-hexahydro-pyridazine-3-carboxylic acid methyl ester

There total 18 articles about (S)-1-[(S)-3-(3-Benzyloxy-phenyl)-2-((S)-2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-propionyl]-hexahydro-pyridazine-3-carboxylic acid methyl 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: 81.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + (3S)-N,N'-bis-(t-butoxycarbonyl)hexahydropyridazine-3-carboxylic acid (156699-39-7) + trifluoroacetic acid (76-05-1) + (S)-tetrahydro-pyridazine-1,2,3-tricarboxylic acid 1,2-di-tert-butyl ester 3-methyl ester (222556-21-0,174497-80-4) + methyl (3S)-1,2-diazinane-3-carboxylate bis(trifluoroacetic acid) salt + (S)-3-(3-(benzyloxy)phenyl)-2-((S)-2-((tert-butoxycarbonyl)amino)-3-methylbutanamido)propanoic acid (222556-20-9) → (S)-1-[(S)-3-(3-Benzyloxy-phenyl)-2-((S)-2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-propionyl]-hexahydro-pyridazine-3-carboxylic acid methyl ester (222556-14-1)

Guidance literature:

diazomethane; (3S)-N,N'-bis-(t-butoxycarbonyl)hexahydropyridazine-3-carboxylic acid; In diethyl ether; at 20 ℃;

trifluoroacetic acid; (S)-tetrahydro-pyridazine-1,2,3-tricarboxylic acid 1,2-di-tert-butyl ester 3-methyl ester; In dichloromethane; at 20 ℃;

methyl (3S)-1,2-diazinane-3-carboxylate bis(trifluoroacetic acid) salt; (S)-3-(3-(benzyloxy)phenyl)-2-((S)-2-((tert-butoxycarbonyl)amino)-3-methylbutanamido)propanoic acid; With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 0 - 20 ℃;

DOI:10.1016/S0040-4039(99)00212-9

Reference yield:

2C2HF3O2*C6H12N2O2 + (S)-3-(3-(benzyloxy)phenyl)-2-((S)-2-((tert-butoxycarbonyl)amino)-3-methylbutanamido)propanoic acid (222556-20-9) → C32H44N4O7 + (S)-1-[(S)-3-(3-Benzyloxy-phenyl)-2-((S)-2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-propionyl]-hexahydro-pyridazine-3-carboxylic acid methyl ester (222556-14-1)

Guidance literature:

(S)-3-(3-(benzyloxy)phenyl)-2-((S)-2-((tert-butoxycarbonyl)amino)-3-methylbutanamido)propanoic acid; With N-ethyl-N,N-diisopropylamine; 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 20 ℃; for 0.166667h;

2C₂HF₃O₂*C₆H₁₂N₂O₂; In N,N-dimethyl-formamide; at 20 ℃; for 2h; Overall yield = 76 %; Overall yield = 48 mg; diastereoselective reaction;

DOI:10.1080/00397911.2014.947653

Reference yield:

3-(3-hydroxyphenyl)-propanoic acid (621-54-5) → (S)-1-[(S)-3-(3-Benzyloxy-phenyl)-2-((S)-2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-propionyl]-hexahydro-pyridazine-3-carboxylic acid methyl ester (222556-14-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 71 percent / K₂CO₃; NaOH / 60 °C

2.1: 82 percent / PivCl; Et₃N / tetrahydrofuran / -78 °C

3.1: KHMDS; trisyl azide / tetrahydrofuran / -78 °C

3.2: 59 percent / trisyl azide / acetic acid / 20 °C

4.1: 100 percent / H₂ / Pd-BaSO₄ / ethyl acetate

5.1: CH₂Cl₂ / 0 °C

5.2: 83 percent / NMM; HOBT; EDCl / dimethylformamide / 0 - 20 °C

6.1: 77 percent / LiOH; H₂O₂ / tetrahydrofuran; H₂O / 0 °C

7.1: diethyl ether / 20 °C

7.2: CH₂Cl₂ / 20 °C

7.3: 81 percent / NMM; HOBT; EDCl / dimethylformamide / 0 - 20 °C

With lithium hydroxide; sodium hydroxide; 2,4,6-Triisopropylbenzenesulfonyl azide; hydrogen; dihydrogen peroxide; pivaloyl chloride; potassium hexamethylsilazane; potassium carbonate; triethylamine; palladium on barium sulfate; In tetrahydrofuran; diethyl ether; dichloromethane; water; ethyl acetate; 1.1: Etherification / 2.1: Condensation / 3.1: Substitution / 3.2: Hydrolysis / 4.1: Catalytic hydrogenation / 5.1: Decarbonylation / 5.2: Condensation / 6.1: Hydrolysis / 7.1: Methylation / 7.2: Decarbonylation / 7.3: Condensation;

DOI:10.1016/S0040-4039(99)00212-9

upstream raw materials:

diazomethane

(3S)-N,N'-bis-(t-butoxycarbonyl)hexahydropyridazine-3-carboxylic acid

trifluoroacetic acid

(S)-tetrahydro-pyridazine-1,2,3-tricarboxylic acid 1,2-di-tert-butyl ester 3-methyl ester