3-Acetyl-N-benzyloxycarbonyl-L-tyrosine Methyl Ester

Base Information

• Chemical Name: 3-Acetyl-N-benzyloxycarbonyl-L-tyrosine Methyl Ester
• CAS No.: 110774-03-3
• Molecular Formula: C20H21NO6
• Molecular Weight: 371.39
• DSSTox Substance ID: DTXSID60473312
• Nikkaji Number: J1.649.876I
• Wikidata: Q82302638
• Mol file: 110774-03-3.mol

Synonyms:110774-03-3;3-Acetyl-N-benzyloxycarbonyl-L-tyrosine Methyl Ester;3-Acetyl-N-Cbz-L-tyrosine Methyl Ester;methyl (2S)-3-(3-acetyl-4-hydroxyphenyl)-2-(phenylmethoxycarbonylamino)propanoate;Methyl (S)-3-(3-acetyl-4-hydroxyphenyl)-2-(((benzyloxy)carbonyl)amino)propanoate;3-Acetyl-N-[(phenylmethoxy)carbonyl]-L-tyrosine Methyl Ester;DTXSID60473312;AC9128;CS-0106915;J-002479;Methyl 3-acetyl-N-[(benzyloxy)carbonyl]-L-tyrosinate

Chemical Property of 3-Acetyl-N-benzyloxycarbonyl-L-tyrosine Methyl Ester

Chemical Property:

• Melting Point: 95 °C
• Boiling Point: 577.3±50.0 °C(Predicted)
• PKA: 9.98±0.20(Predicted)
• PSA: 105.42000
• Density: 1.258±0.06 g/cm3(Predicted)
• LogP: 2.80970
• Solubility.: Dichloromethane, Ethyl Acetate
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 9
• Exact Mass: 371.13688739
• Heavy Atom Count: 27
• Complexity: 517

Purity/Quality:

98%Min ^*data from raw suppliers

3-Acetyl-N-benzyloxycarbonyl-L-tyrosine Methyl Ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1=C(C=CC(=C1)CC(C(=O)OC)NC(=O)OCC2=CC=CC=C2)O
• Isomeric SMILES: CC(=O)C1=C(C=CC(=C1)C[C@@H](C(=O)OC)NC(=O)OCC2=CC=CC=C2)O

Technology Process of 3-Acetyl-N-benzyloxycarbonyl-L-tyrosine Methyl Ester

There total 4 articles about 3-Acetyl-N-benzyloxycarbonyl-L-tyrosine 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: 98.0%

benzyl chloroformate (501-53-1,94274-21-2) + methyl (S)-3-(3-acetyl-4-hydroxyphenyl)-2-aminopropanoate monohydrochloride (57085-32-2) → L-3-(3-acetyl-4-hydroxyphenyl)-N-(benzyloxycarbonyl)alanine methyl ester (110774-03-3)

Guidance literature:

With sodium carbonate; In diethyl ether; water; at 25 ℃; for 1h;

Reference yield:

(S)-3-(3-acetyl-4-hydroxyphenyl)-2-aminopropanoic acid hydrochloride (32404-28-7) → L-3-(3-acetyl-4-hydroxyphenyl)-N-(benzyloxycarbonyl)alanine methyl ester (110774-03-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / SOCl₂ / Heating

2: 93 percent / aq. Na₂CO₃ / diethyl ether / 3 h / 25 °C

With thionyl chloride; sodium carbonate; In diethyl ether; 1: Fischer esterification;

DOI:10.1021/jm050910x

Reference yield:

L-tyrosine (60-18-4,18875-48-4,25619-78-7,30704-25-7) → L-3-(3-acetyl-4-hydroxyphenyl)-N-(benzyloxycarbonyl)alanine methyl ester (110774-03-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 67 percent / AlCl₃ / nitrobenzene / 6 h / 100 °C

2: 74 percent / SOCl₂ / Heating

3: 93 percent / aq. Na₂CO₃ / diethyl ether / 3 h / 25 °C

With aluminium trichloride; thionyl chloride; sodium carbonate; In diethyl ether; nitrobenzene; 1: Friedel-Crafts acylation / 2: Fischer esterification;

DOI:10.1021/jm050910x

upstream raw materials:

benzyl chloroformate

methyl (S)-3-(3-acetyl-4-hydroxyphenyl)-2-aminopropanoate monohydrochloride

L-tyrosine

(S)-3-(3-acetyl-4-hydroxyphenyl)-2-aminopropanoic acid hydrochloride

Downstream raw materials:

L-3-(3-acetyl-4-(benzyloxy)phenyl)-N-(benzyloxycarbonyl)alanine methyl ester

(R)-3-(3-Acetyl-4-benzyloxy-phenyl)-2-benzyloxycarbonylamino-propionic acid methyl ester

3-acetyl-N,O-dimethyl-N-<(phenylmethoxy)carbonyl>-L-tyrosine methyl ester

3-acetyl-O-methyl-N-<(phenylmethoxy)carbonyl>-L-tyrosine methyl ester

Refernces

• 1、 Song, Yan-Li,Peach, Megan L.,Roller, Peter P.,Qiu, Su,Wang, Shaomeng,Long, Ya-Qiu. "Discovery of a novel nonphosphorylated pentapeptide motif displaying high affinity for Grb2-SH2 domain by the utilization of 3′-substituted tyrosine derivatives". . p. 1585 - 1596. Retrieved 2007/10/03.
• 2、 Boger, Dale L.,Yohannes, Daniel. "Selectively Protected L-Dopa Derivatives: Application of the Benzylic Hydroperoxide Rearrangement". . p. 5283 - 5286. Retrieved 2007/10/02.