glycylphenylalanylmethioninamide hydrochloride

Base Information

• Chemical Name: glycylphenylalanylmethioninamide hydrochloride
• CAS No.: 75189-51-4
• Molecular Formula: C₁₆H₂₄N₄O₃S*ClH
• Molecular Weight: 388.918
• Mol file: 75189-51-4.mol

Synonyms:glycylphenylalanylmethioninamide hydrochloride

Chemical Property of glycylphenylalanylmethioninamide hydrochloride

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of glycylphenylalanylmethioninamide hydrochloride

There total 5 articles about glycylphenylalanylmethioninamide hydrochloride 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: 85.0%

MCA-Phe-Met-OMe (75189-50-3) → glycylphenylalanylmethioninamide hydrochloride (75189-51-4)

Guidance literature:

With ammonia; In methanol; for 48h; Ambient temperature;

Reference yield:

{[(S)-1-((S)-1-Carbamoyl-3-methylsulfanyl-propylcarbamoyl)-2-phenyl-ethylcarbamoyl]-methyl}-carbamic acid tert-butyl ester (66959-98-6) → glycylphenylalanylmethioninamide hydrochloride (75189-51-4)

Guidance literature:

With hydrogenchloride; at 25 ℃; for 0.5h; Yield given;

DOI:10.1021/jm00354a006

Reference yield:

Gly-Phe-OH (3321-03-7) → glycylphenylalanylmethioninamide hydrochloride (75189-51-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / 1N NaOH / tetrahydrofuran / 2.25 h / 25 °C

2: 1.) isobutyl chloroformate, N-methylmorpholine, 2.) Et₃N / 1.) THF, -20 deg C, 20 min, 2.) THF, water, RT, 2.5 h

3: 15percent ethanolic HCl / 0.5 h / 25 °C

With 4-methyl-morpholine; hydrogenchloride; sodium hydroxide; triethylamine; isobutyl chloroformate; In tetrahydrofuran;

DOI:10.1021/jm00354a006

upstream raw materials:

{[(S)-1-((S)-1-Carbamoyl-3-methylsulfanyl-propylcarbamoyl)-2-phenyl-ethylcarbamoyl]-methyl}-carbamic acid tert-butyl ester

MCA-Phe-Met-OMe

(S)-2-(2-chloroacetamido)-4-methylpentanoic acid

Gly-Phe-OH

Downstream raw materials:

(+)-(2S,6S,11S)-<(1,2,3,4,5,6-hexahydro-8-hydroxy-3,6,11-trimethyl-2,6-methano-3-benzazocin-2-yl)carbonyl>glycylglycylphenylalanylmethioninamide

(-)-(2R,6R,11R)-<(1,2,3,4,5,6-hexahydro-8-hydroxy-3,6,11-trimethyl-2,6-methano-3-benzazocin-2-yl)carbonyl>glycylglycylphenylalanylmethioninamide

Refernces

• 1、 Lipkowski, Andrzej W.,Majewski, Tadeusz,Drabarek, Stefania. "RAPID LARGE-SCALE SYNTHESIS OF GLYCYL-PEPTIDE AMIDES". . p. 373 - 374. Retrieved 2007/10/02.