(S)-2-((S)-2-tert-Butoxycarbonylamino-3-methyl-butyrylamino)-3-(3-hydroxy-phenyl)-propionic acid

Base Information

• Chemical Name: (S)-2-((S)-2-tert-Butoxycarbonylamino-3-methyl-butyrylamino)-3-(3-hydroxy-phenyl)-propionic acid
• CAS No.: 234122-58-8
• Molecular Formula: C₁₉H₂₈N₂O₆
• Molecular Weight: 380.441
• Mol file: 234122-58-8.mol

Synonyms:(S)-2-((S)-2-tert-Butoxycarbonylamino-3-methyl-butyrylamino)-3-(3-hydroxy-phenyl)-propionic acid

Chemical Property of (S)-2-((S)-2-tert-Butoxycarbonylamino-3-methyl-butyrylamino)-3-(3-hydroxy-phenyl)-propionic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-((S)-2-tert-Butoxycarbonylamino-3-methyl-butyrylamino)-3-(3-hydroxy-phenyl)-propionic acid

There total 7 articles about (S)-2-((S)-2-tert-Butoxycarbonylamino-3-methyl-butyrylamino)-3-(3-hydroxy-phenyl)-propionic 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: 89.0%

(S)-2-((S)-2-tert-Butoxycarbonylamino-3-methyl-butyrylamino)-3-(3-hydroxy-phenyl)-propionic acid methyl ester (234122-57-7) → (S)-2-((S)-2-tert-Butoxycarbonylamino-3-methyl-butyrylamino)-3-(3-hydroxy-phenyl)-propionic acid (234122-58-8)

Guidance literature:

With lithium hydroxide; water; In tetrahydrofuran; at 0 - 25 ℃; for 1.5h;

Reference yield:

(S)-methyl 2-((benzyloxycarbonyl)amino)-3-(3-hydroxyphenyl)propanoate (234122-64-6) → (S)-2-((S)-2-tert-Butoxycarbonylamino-3-methyl-butyrylamino)-3-(3-hydroxy-phenyl)-propionic acid (234122-58-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / H₂ / Pd/C / methanol / 12 h / 25 °C / 760.05 Torr

2: 78 percent / EDC; HOAt / CH₂Cl₂ / 3 h / 20 °C

3: 89 percent / aq. LiOH / tetrahydrofuran / 1.5 h / 0 °C

With lithium hydroxide; 1-hydroxy-7-aza-benzotriazole; hydrogen; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; 1: Hydrogenolysis / 2: Acylation / 3: Hydrolysis;

DOI:10.1021/ja994285v

Reference yield:

(Z)-methyl 2-((benzyloxycarbonyl)amino)-3-(3-hydroxyphenyl)acrylate (234122-56-6) → (S)-2-((S)-2-tert-Butoxycarbonylamino-3-methyl-butyrylamino)-3-(3-hydroxy-phenyl)-propionic acid (234122-58-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / H₂ / [(S,S)-Et-DuP-Rh]⁺TfO^- / methanol / 96 h / 3102.97 Torr

2: 96 percent / H₂ / Pd/C / methanol / 12 h / 25 °C / 760.05 Torr

3: 78 percent / EDC; HOAt / CH₂Cl₂ / 3 h / 20 °C

4: 89 percent / aq. LiOH / tetrahydrofuran / 1.5 h / 0 °C

With lithium hydroxide; 1-hydroxy-7-aza-benzotriazole; hydrogen; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; palladium on activated charcoal; (+)-1,2-bis((2S,5S)-2,5-diethylphospholano)benzene(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate; In tetrahydrofuran; methanol; dichloromethane; 1: stereoselective hydrogenation / 2: Hydrogenolysis / 3: Acylation / 4: Hydrolysis;

DOI:10.1021/ja994285v

upstream raw materials:

(S)-2-((S)-2-tert-Butoxycarbonylamino-3-methyl-butyrylamino)-3-(3-hydroxy-phenyl)-propionic acid methyl ester

t-Boc-L-valine

methyl (S)-2-amino-3-(3-hydroxyphenyl)propanoate

meta-hydroxybenzaldehyde

Downstream raw materials:

(S)-1-[(S)-2-((S)-2-Amino-3-methyl-butyrylamino)-3-(3-hydroxy-phenyl)-propionyl]-hexahydro-pyridazine-3-carboxylic acid (E)-4-iodo-but-3-enyl ester

(R)-1-[(S)-2-((S)-2-Amino-3-methyl-butyrylamino)-3-(3-hydroxy-phenyl)-propionyl]-hexahydro-pyridazine-3-carboxylic acid (E)-4-iodo-but-3-enyl ester

(S)-1-[(S)-2-((S)-2-Amino-3-methyl-butyrylamino)-3-(3-hydroxy-phenyl)-propionyl]-hexahydro-pyridazine-3-carboxylic acid (E)-(S)-4-iodo-1-((E)-2-iodo-1-methyl-vinyl)-but-3-enyl ester

sanglifehrin A ketal