(S)-Ethyl 2-(((benzyloxy)carbonyl)amino)-3-(4-hydroxyphenyl)propanoate

Base Information

• Chemical Name: (S)-Ethyl 2-(((benzyloxy)carbonyl)amino)-3-(4-hydroxyphenyl)propanoate
• CAS No.: 16679-94-0
• Molecular Formula: C19H21 N O5
• Molecular Weight: 343.379
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID20473893
• Nikkaji Number: J1.323.290C
• Wikidata: Q82303570
• Mol file: 16679-94-0.mol

Synonyms:16679-94-0;Z-TYR-OET;(S)-Ethyl 2-(((benzyloxy)carbonyl)amino)-3-(4-hydroxyphenyl)propanoate;ethyl (2S)-3-(4-hydroxyphenyl)-2-(phenylmethoxycarbonylamino)propanoate;Z-L-tyrosine ethyl ester;Ethyl N-[(benzyloxy)carbonyl]-L-tyrosinate;Cbz-L-tyrosine ethyl ester;N-cbz-l-tyrosine ethyl ester;L-Tyrosine, N-[(phenylmethoxy)carbonyl]-, ethyl ester;SCHEMBL11199738;DTXSID20473893;ETHYL (2S)-2-{[(BENZYLOXY)CARBONYL]AMINO}-3-(4-HYDROXYPHENYL)PROPANOATE;MFCD00191167;AKOS016843144;AM82332;Ethyl ((benzyloxy)carbonyl)-L-tyrosinate;A882301;(S)-ethyl 2-(benzyloxycarbonylamino)-3-(4-hydroxyphenyl)propanoate;(S)-Ethyl2-(((benzyloxy)carbonyl)amino)-3-(4-hydroxyphenyl)propanoate

Chemical Property of (S)-Ethyl 2-(((benzyloxy)carbonyl)amino)-3-(4-hydroxyphenyl)propanoate

Chemical Property:

• PSA: 84.86000
• LogP: 3.18370
• Storage Temp.: 2-8°C
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 343.14197277
• Heavy Atom Count: 25
• Complexity: 414

Purity/Quality:

98.5% ^*data from raw suppliers

Z-L-tyrosine ethyl ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOC(=O)C(CC1=CC=C(C=C1)O)NC(=O)OCC2=CC=CC=C2
• Isomeric SMILES: CCOC(=O)[C@H](CC1=CC=C(C=C1)O)NC(=O)OCC2=CC=CC=C2

Technology Process of (S)-Ethyl 2-(((benzyloxy)carbonyl)amino)-3-(4-hydroxyphenyl)propanoate

There total 10 articles about (S)-Ethyl 2-(((benzyloxy)carbonyl)amino)-3-(4-hydroxyphenyl)propanoate 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: 96.0%

L-tyrosine ethyl ester monohydrochloride (4089-07-0) → N-[(phenylmethoxy)carbonyl]-L-tyrosine (16679-94-0)

Guidance literature:

Reference yield: 91.0%

L-tyrosine ethyl ester monohydrochloride (4089-07-0) + benzyl chloroformate (501-53-1,94274-21-2) → N-[(phenylmethoxy)carbonyl]-L-tyrosine (16679-94-0)

Guidance literature:

With sodium carbonate; 0 deg C then room temp.;

DOI:10.1021/jo00088a009

Reference yield: 86.0%

ethanol (64-17-5) + N-α-benzyloxycarbonyl-DL-tyrosine (5618-98-4) → N-[(phenylmethoxy)carbonyl]-L-tyrosine (16679-94-0) + N-α-benzyloxycarbonyl-D-tyrosine (64205-12-5)

Guidance literature:

With citrate buffer; DL-cysteine hydrochloride; papain; at 50 ℃; for 24h;

upstream raw materials:

L-tyrosine ethyl ester monohydrochloride

benzyl chloroformate

L-tyrosine ethyl ester

ethanol

Downstream raw materials:

Z-Tyr-Gly-Gly-OEt

4-nitro-phenol

ethyl 2-(tert-butoxycarbonylamino)acetate

Z-L-Tyr-OH

Refernces

• 1、 Kohno, Harumichi,Iwakuma, Takeo,Yamada, Koichiro. "A simple and efficient procedure for the synthesis of optically active 4-methoxy-α-methylphenylethylamine from tyrosine". . p. 1935 - 1945. Retrieved 2007/10/03.
• 2、 Pearson, Anthony J.,Lee, Kieseung. "A Formal Total Synthesis of the ACE Inhibitor K-13. An Application of Arene-Ruthenium Chemistry to Complex Chemical Synthesis". . p. 2304 - 2313. Retrieved 2007/10/02.