5-cyclohexyl-3-hydroxy-N-(2-morpholin-4-ylethyl)-4-[[2-[[4-morpholin-4-yl-2-(naphthalen-1-ylmethyl)-4-oxobutanoyl]amino]-3-(1,3-thiazol-4-yl)propanoyl]amino]pentanamide

Base Information

• Chemical Name: 5-cyclohexyl-3-hydroxy-N-(2-morpholin-4-ylethyl)-4-[[2-[[4-morpholin-4-yl-2-(naphthalen-1-ylmethyl)-4-oxobutanoyl]amino]-3-(1,3-thiazol-4-yl)propanoyl]amino]pentanamide
• CAS No.: 116326-39-7
• Molecular Formula: C₄₂H₅₈N₆O₇S
• Molecular Weight: 791.025
• Mol file: 116326-39-7.mol

Synonyms:ES 6864;ES-6864;N-(3-morpholinocarbonyl-2-(1-npahthylmethyl)propionyl)-(4-thiazolyl)-L-alanyl-cyclostatine-(2-morpholinoethyl)amide

Chemical Property of 5-cyclohexyl-3-hydroxy-N-(2-morpholin-4-ylethyl)-4-[[2-[[4-morpholin-4-yl-2-(naphthalen-1-ylmethyl)-4-oxobutanoyl]amino]-3-(1,3-thiazol-4-yl)propanoyl]amino]pentanamide

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 1088.5°C at 760 mmHg
• Flash Point: 612.1°C
• PSA: 201.14000
• Density: 1.242g/cm³
• LogP: 5.48270
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 18
• Exact Mass: 790.40876938
• Heavy Atom Count: 56
• Complexity: 1250

Purity/Quality:

99% ^*data from raw suppliers

ES 6864 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(CC1)CC(C(CC(=O)NCCN2CCOCC2)O)NC(=O)C(CC3=CSC=N3)NC(=O)C(CC4=CC=CC5=CC=CC=C54)CC(=O)N6CCOCC6

Technology Process of 5-cyclohexyl-3-hydroxy-N-(2-morpholin-4-ylethyl)-4-[[2-[[4-morpholin-4-yl-2-(naphthalen-1-ylmethyl)-4-oxobutanoyl]amino]-3-(1,3-thiazol-4-yl)propanoyl]amino]pentanamide

There total 17 articles about 5-cyclohexyl-3-hydroxy-N-(2-morpholin-4-ylethyl)-4-[[2-[[4-morpholin-4-yl-2-(naphthalen-1-ylmethyl)-4-oxobutanoyl]amino]-3-(1,3-thiazol-4-yl)propanoyl]amino]pentanamide 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: 71.0%

(2R)-3-(Morpholinocarbonyl)-2-(1-naphthylmethyl)-propionic acid (119434-65-0) + (3S,4S)-4-((S)-2-Amino-3-thiazol-4-yl-propionylamino)-5-cyclohexyl-3-hydroxy-pentanoic acid (2-morpholin-4-yl-ethyl)-amide (119357-93-6) → ES-6864 (116326-39-7,119399-16-5,121349-88-0,129313-65-1)

Guidance literature:

With triethylamine; diethyl dicarbonate; In tetrahydrofuran; at 0 ℃; for 8h;

DOI:10.1248/cpb.38.103

Reference yield:

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → ES-6864 (116326-39-7,119399-16-5,121349-88-0,129313-65-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 1) N,N'-carbonyldiimidazole / 1) tetrahydrofuran, 30 min, 2) tetrahydrofuran, dimethyl sulfoxide, 4h, room temp.

2: 97 percent / H₂ / RuBr₂<(R)-binap> / ethanol / 145 h / 20 °C / 76000.1 Torr

3: 96 percent / aq. potassium hydroxide / dioxane / 8 h / 0 °C

4: H₂ / 5percent Rh-Al₂O₃ / ethanol / 16 h / 3040 - 3800 Torr

5: 96 percent / DEPC, triethylamine / tetrahydrofuran / 6 h / 0 °C

6: 4N HCl / dioxane / 0.5 h / Ambient temperature

7: 91 percent / DEPC, triethylamine / tetrahydrofuran / 6 h / 0 °C

8: 4N HCl / dioxane / 0.5 h / Ambient temperature

9: 71 percent / DEPC, triethylamine / tetrahydrofuran / 8 h / 0 °C

With hydrogenchloride; potassium hydroxide; hydrogen; triethylamine; diethyl dicarbonate; 1,1'-carbonyldiimidazole; [(R)-BINAP]RuBr₂; rhodium on alumina; In tetrahydrofuran; 1,4-dioxane; ethanol;

DOI:10.1248/cpb.38.103

Reference yield:

3-(1-naphthalenyl)propionyl chloride (99124-56-8) → ES-6864 (116326-39-7,119399-16-5,121349-88-0,129313-65-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 1) n-BuLi / 1) tetrahydrofuran, hexane, -78 deg C, 30 min, 2) tetrahydrofuran, 1h

2: 1) lithium diisopropylamide / 1) tetrahydrofuran, hexane, -78 deg C, 1h, 2) tetrahydrofuran, 5h, -78 up to 0 deg C

3: H₂ / 10percent Pd-C / ethanol / Ambient temperature

4: 97 percent / DEPC, triethylamine / tetrahydrofuran / 2 h / 0 °C

5: 83 percent / LiOH*H₂O / tetrahydrofuran; H₂O / 3 h / 0 °C

6: 71 percent / DEPC, triethylamine / tetrahydrofuran / 8 h / 0 °C

With lithium hydroxide; n-butyllithium; hydrogen; triethylamine; diethyl dicarbonate; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; ethanol; water;

DOI:10.1248/cpb.38.103

upstream raw materials:

(2R)-3-(Morpholinocarbonyl)-2-(1-naphthylmethyl)-propionic acid

(3S,4S)-4-((S)-2-Amino-3-thiazol-4-yl-propionylamino)-5-cyclohexyl-3-hydroxy-pentanoic acid (2-morpholin-4-yl-ethyl)-amide

4-(2-AMINOETHYL)MORPHOLINE

N-tert-butoxycarbonyl-L-phenylalanine

Refernces