N-<(1,1-Dimethylethoxy)carbonyl>-4-chloro-L-phenylalanine 2-bromoethyl ester

Base Information

• Chemical Name: N-<(1,1-Dimethylethoxy)carbonyl>-4-chloro-L-phenylalanine 2-bromoethyl ester
• CAS No.: 159750-09-1
• Molecular Formula: C₁₆H₂₁BrClNO₄
• Molecular Weight: 406.704
• Mol file: 159750-09-1.mol

Synonyms:

Chemical Property of N-<(1,1-Dimethylethoxy)carbonyl>-4-chloro-L-phenylalanine 2-bromoethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-<(1,1-Dimethylethoxy)carbonyl>-4-chloro-L-phenylalanine 2-bromoethyl ester

There total 9 articles about N-<(1,1-Dimethylethoxy)carbonyl>-4-chloro-L-phenylalanine 2-bromoethyl 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: 76.0%

Boc-p-chloro-L-Phe-OH (51301-86-1,57292-44-1,129101-26-4,68090-88-0) + 2-bromoethanol (540-51-2) → N-<(1,1-Dimethylethoxy)carbonyl>-4-chloro-L-phenylalanine 2-bromoethyl ester (159750-09-1)

Guidance literature:

With pyridine; dicyclohexyl-carbodiimide; 1.) CH₂Cl₂, 0 deg C, 10 min, 2.) 0 deg C, overnight;

DOI:10.1021/jo00088a009

Reference yield:

3-(4-chlorophenyl)propanoic acid (2019-34-3) → N-<(1,1-Dimethylethoxy)carbonyl>-4-chloro-L-phenylalanine 2-bromoethyl ester (159750-09-1)

Guidance literature:

Multi-step reaction with 7 steps

1: Et₃N / tetrahydrofuran / 1.) -78 deg C, 15 min, 2.) 0 deg C, 45 min

2: n-BuLi / 1.) THF, hexane, -78 deg C, 20 min, 2.) -78 deg C, 15 min and room temp., 10 h

3: 1.) KHMDS, 2.) trisyl azide / 1.) THF, toluene, -78 deg C, 30 min, 2.) THF, -78 deg C, 2 min

4: H₂, 5 N HCl / 10percent Pd-C / tetrahydrofuran; methanol / 8 h / 760 Torr / Ambient temperature

5: K₂CO₃ / tetrahydrofuran; H₂O / Ambient temperature

6: 77 percent / aq. LiOH / tetrahydrofuran / 1 h / 0 °C

7: 76 percent / pyridine, DCC / 1.) CH₂Cl₂, 0 deg C, 10 min, 2.) 0 deg C, overnight

With pyridine; hydrogenchloride; lithium hydroxide; n-butyllithium; 2,4,6-Triisopropylbenzenesulfonyl azide; hydrogen; potassium hexamethylsilazane; potassium carbonate; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; water;

DOI:10.1021/jo00088a009

Reference yield:

3-(4-chlorophenyl)prop-2-enoic acid (1615-02-7,940-62-5) → N-<(1,1-Dimethylethoxy)carbonyl>-4-chloro-L-phenylalanine 2-bromoethyl ester (159750-09-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 88 percent / H₂ / 10percent Pd-C / tetrahydrofuran / 4 h / Ambient temperature

2: Et₃N / tetrahydrofuran / 1.) -78 deg C, 15 min, 2.) 0 deg C, 45 min

3: n-BuLi / 1.) THF, hexane, -78 deg C, 20 min, 2.) -78 deg C, 15 min and room temp., 10 h

4: 1.) KHMDS, 2.) trisyl azide / 1.) THF, toluene, -78 deg C, 30 min, 2.) THF, -78 deg C, 2 min

5: H₂, 5 N HCl / 10percent Pd-C / tetrahydrofuran; methanol / 8 h / 760 Torr / Ambient temperature

6: K₂CO₃ / tetrahydrofuran; H₂O / Ambient temperature

7: 77 percent / aq. LiOH / tetrahydrofuran / 1 h / 0 °C

8: 76 percent / pyridine, DCC / 1.) CH₂Cl₂, 0 deg C, 10 min, 2.) 0 deg C, overnight

With pyridine; hydrogenchloride; lithium hydroxide; n-butyllithium; 2,4,6-Triisopropylbenzenesulfonyl azide; hydrogen; potassium hexamethylsilazane; potassium carbonate; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; water;

DOI:10.1021/jo00088a009

upstream raw materials:

Boc-p-chloro-L-Phe-OH

2-bromoethanol

3-(4-chlorophenyl)propanoic acid

di-tert-butyl dicarbonate

Downstream raw materials:

(S)-3-<4-<2-<<(1,1-Dimethylethoxy)carbonyl>amino>-3-oxo-3-(2-iodoethoxy)propyl>phenoxy>-O-methyl-N--L-tyrosinyl>-L-tyrosine α-methyl ester

(S)-3-<4-<2-Carboxy-2-<<(1,1-dimethylethoxy)carbonyl>amino>ethyl>phenoxy>-O-methyl-N--L-tyrosinyl>-L-tyrosine α-methyl ester

(S)-3-<4-<2-<<(1,1-Dimethylethoxy)carbonyl>amino>-3-oxo-3-(2-bromoethoxy)propyl>phenoxy>-O-methyl-N--L-tyrosinyl>-L-tyrosine α-methyl ester

Refernces