(3S)-4-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(3R)-1-[(2S)-1-[[(2S)-1-amino-4-methylsulfanyl-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]-2-oxopyrrolidin-3-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-[[(2S)-2,6-diaminohexanoyl]amino]-4-oxobutanoic acid

Base Information

• Chemical Name: (3S)-4-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(3R)-1-[(2S)-1-[[(2S)-1-amino-4-methylsulfanyl-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]-2-oxopyrrolidin-3-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-[[(2S)-2,6-diaminohexanoyl]amino]-4-oxobutanoic acid
• CAS No.: 137593-52-3
• Deprecated CAS: 136548-07-7,136218-59-2
• Molecular Formula: C₄₂H₆₈N₁₀O₁₁S
• Molecular Weight: 921.128
• Nikkaji Number: J515.480D
• Mol file: 137593-52-3.mol

Synonyms:3-Lys-8-Gly-R-lactam-9-Leu-neurokinin A (3-10);GR 64349;GR-64349;neurokinin A (3-10), Lys(3)-Gly(8)-R-lactam-Leu(9)-;neurokinin A (3-10), lysyl(3)-glycyl(8)-R-lactam-leucine(9)-

Chemical Property of (3S)-4-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(3R)-1-[(2S)-1-[[(2S)-1-amino-4-methylsulfanyl-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]-2-oxopyrrolidin-3-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-[[(2S)-2,6-diaminohexanoyl]amino]-4-oxobutanoic acid

Chemical Property:

• Boiling Point: 1342.8°Cat760mmHg
• PKA: 4.13±0.10(Predicted)
• Flash Point: 765.9°C
• PSA: 372.87000
• Density: 1.31g/cm³
• LogP: 1.98680
• Storage Temp.: −20°C
• XLogP3: -3.1
• Hydrogen Bond Donor Count: 11
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 29
• Exact Mass: 920.47897420
• Heavy Atom Count: 64
• Complexity: 1600

Purity/Quality:

99% ^*data from raw suppliers

GR 64349 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)CC(C(=O)NC(CCSC)C(=O)N)N1CCC(C1=O)NC(=O)C(C(C)C)NC(=O)C(CC2=CC=CC=C2)NC(=O)C(CO)NC(=O)C(CC(=O)O)NC(=O)C(CCCCN)N
• Isomeric SMILES: CC(C)C[C@@H](C(=O)N[C@@H](CCSC)C(=O)N)N1CC[C@H](C1=O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC2=CC=CC=C2)NC(=O)[C@H](CO)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CCCCN)N
• Uses: GR 64349 acts as a potent and selective agonist at the NK-2 tachykinin receptor. Initiates changes in the colon, intestine and spinal cord.

Technology Process of (3S)-4-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(3R)-1-[(2S)-1-[[(2S)-1-amino-4-methylsulfanyl-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]-2-oxopyrrolidin-3-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-[[(2S)-2,6-diaminohexanoyl]amino]-4-oxobutanoic acid

There total 4 articles about (3S)-4-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(3R)-1-[(2S)-1-[[(2S)-1-amino-4-methylsulfanyl-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]-2-oxopyrrolidin-3-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-[[(2S)-2,6-diaminohexanoyl]amino]-4-oxobutanoic 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:

(R)-2-<3-<(tert-butoxycarbonyl)amino>-2-oxo-1-pyrrolidinyl>-(S)-4-methylpentanoic acid methyl ester (124202-00-2) → L-lysyl-L-α-aspartyl-L-seryl-L-phenylalanyl-L-valyl-(αS,3R)-3-amino-α-(2-methylpropyl)-2-oxo-1-pyrrolidineacetyl-L-methioninamide (137593-52-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / 2 M aq. NaOH / methanol / 18 h / 0 °C

2: 57 percent / DCC / dimethylformamide / 3 h / 20 °C

With sodium hydroxide; dicyclohexyl-carbodiimide; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/jm00100a027

Reference yield:

(2S)-2-<(3R)-3-<(tert-butoxycarbonyl)amino>-2-oxopyrrolidin-1-yl>-4-methylpentanoic acid (82611-48-1) → L-lysyl-L-α-aspartyl-L-seryl-L-phenylalanyl-L-valyl-(αS,3R)-3-amino-α-(2-methylpropyl)-2-oxo-1-pyrrolidineacetyl-L-methioninamide (137593-52-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 57 percent / DCC / dimethylformamide / 3 h / 20 °C

With dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide;

DOI:10.1021/jm00100a027

Reference yield:

N-(tert-butoxycarbonyl)-D-methionyl-L-leucine methyl ester (82611-46-9) → L-lysyl-L-α-aspartyl-L-seryl-L-phenylalanyl-L-valyl-(αS,3R)-3-amino-α-(2-methylpropyl)-2-oxo-1-pyrrolidineacetyl-L-methioninamide (137593-52-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) CH₃I, 2.) NaH / 1.) 5 d, 2.) DMF, -40 - 3 deg C, 45 min

2: 94 percent / 2 M aq. NaOH / methanol / 18 h / 0 °C

3: 57 percent / DCC / dimethylformamide / 3 h / 20 °C

With sodium hydroxide; sodium hydride; dicyclohexyl-carbodiimide; methyl iodide; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/jm00100a027

upstream raw materials:

Fmoc-Val-OPfp

N-α-Fmoc-L-phenylalanine pentafluorophenyl ester

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine

(R)-2-<3-<(tert-butoxycarbonyl)amino>-2-oxo-1-pyrrolidinyl>-(S)-4-methylpentanoic acid pentafluorophenyl ester