(2R)-2-(acryloylamino)-3-(3-chloro-4-methoxyphenyl)propanoic acid

Base Information

• Chemical Name: (2R)-2-(acryloylamino)-3-(3-chloro-4-methoxyphenyl)propanoic acid
• CAS No.: 905309-58-2
• Molecular Formula: C₁₃H₁₄ClNO₄
• Molecular Weight: 283.711
• Mol file: 905309-58-2.mol

Synonyms:(2R)-2-(acryloylamino)-3-(3-chloro-4-methoxyphenyl)propanoic acid

Chemical Property of (2R)-2-(acryloylamino)-3-(3-chloro-4-methoxyphenyl)propanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R)-2-(acryloylamino)-3-(3-chloro-4-methoxyphenyl)propanoic acid

There total 6 articles about (2R)-2-(acryloylamino)-3-(3-chloro-4-methoxyphenyl)propanoic 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: 99.0%

methyl (2R)-2-(acryloylamino)-3-(3-chloro-4-methoxyphenyl)propanoate (905309-57-1) → (2R)-2-(acryloylamino)-3-(3-chloro-4-methoxyphenyl)propanoic acid (905309-58-2)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; methanol; water; at 20 ℃; for 4h;

DOI:10.1021/ol0609356

Reference yield:

tyrosine (556-02-5,18875-48-4,25619-78-7,30704-25-7) → (2R)-2-(acryloylamino)-3-(3-chloro-4-methoxyphenyl)propanoic acid (905309-58-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 94 percent / glacial acetic acid; SO₂Cl₂ / 2 h / 20 °C

2: 99 percent / NaOH / H₂O; 2-methyl-propan-2-ol / 16 h / 20 °C

3: 96 percent / K₂CO₃ / acetonitrile / 4 h / Heating

4: 84 percent / TFA / CH₂Cl₂ / 3 h / 20 °C

5: 96 percent / DIEA / CH₂Cl₂ / 0 - 20 °C

6: 99 percent / LiOH / tetrahydrofuran; methanol; H₂O / 4 h / 20 °C

With lithium hydroxide; sodium hydroxide; sulfuryl dichloride; potassium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile; tert-butyl alcohol;

DOI:10.1021/ol0609356

Reference yield:

(2R)-2-[(tert-butoxycarbonyl)amino]-3-(3-chloro-4-hydroxyphenyl)propanoic acid (478183-57-2) → (2R)-2-(acryloylamino)-3-(3-chloro-4-methoxyphenyl)propanoic acid (905309-58-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 96 percent / K₂CO₃ / acetonitrile / 4 h / Heating

2: 84 percent / TFA / CH₂Cl₂ / 3 h / 20 °C

3: 96 percent / DIEA / CH₂Cl₂ / 0 - 20 °C

4: 99 percent / LiOH / tetrahydrofuran; methanol; H₂O / 4 h / 20 °C

With lithium hydroxide; potassium carbonate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile;

DOI:10.1021/ol0609356

upstream raw materials:

methyl (2R)-2-(acryloylamino)-3-(3-chloro-4-methoxyphenyl)propanoate

tyrosine

(2R)-2-[(tert-butoxycarbonyl)amino]-3-(3-chloro-4-hydroxyphenyl)propanoic acid

methyl (2R)-2-[(tert-butoxycarbonyl)amino]-3-(3-chloro-4-methoxyphenyl)propanoate

Downstream raw materials:

allyl (2S)-2-({3-[(N-acryloyl-3-chloro-O-methyl-D-tyrosyl)amino]-2,2-dimethylpropanoyl}oxy)-4-methylpentanoate

(3S,10R,16S)-16-[(2Z)-2-benzylidene-4-phenylbut-3-ynyl]-10-(3-chloro-4-methoxybenzyl)-3-isobutyl-6,6-dimethyl-1,4-dioxa-8,11-diazacyclohexadec-13-ene-2,5,9,12-tetrone

(1S,3Z)-1-allyl-4-iodo-4-phenylbut-3-enyl (2S)-2-({3-[(N-acryloyl-3-chloro-O-methyl-D-tyrosyl)amino]-2,2-dimethylpropanoyl}oxy)-4-methylpentanoate

(1R,3Z)-1-allyl-4-iodo-4-phenylbut-3-enyl (2S)-2-({3-[(N-acryloyl-3-chloro-O-methyl-D-tyrosyl)amino]-2,2-dimethylpropanoyl}oxy)-4-methylpentanoate