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

Base Information

• Chemical Name: methyl (2R)-2-(acryloylamino)-3-(3-chloro-4-methoxyphenyl)propanoate
• CAS No.: 905309-57-1
• Molecular Formula: C₁₄H₁₆ClNO₄
• Molecular Weight: 297.738
• Mol file: 905309-57-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about methyl (2R)-2-(acryloylamino)-3-(3-chloro-4-methoxyphenyl)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%

acryloyl chloride (814-68-6,25189-84-8) + methyl (2R)-2-amino-3-(3-chloro-4-methoxyphenyl)propanoate (704870-54-2) → methyl (2R)-2-(acryloylamino)-3-(3-chloro-4-methoxyphenyl)propanoate (905309-57-1)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/ol0609356

Reference yield:

tyrosine (556-02-5,18875-48-4,25619-78-7,30704-25-7) → methyl (2R)-2-(acryloylamino)-3-(3-chloro-4-methoxyphenyl)propanoate (905309-57-1)

Guidance literature:

Multi-step reaction with 5 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

With sodium hydroxide; sulfuryl dichloride; potassium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In 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) → methyl (2R)-2-(acryloylamino)-3-(3-chloro-4-methoxyphenyl)propanoate (905309-57-1)

Guidance literature:

Multi-step reaction with 3 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

With potassium carbonate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In dichloromethane; acetonitrile;

DOI:10.1021/ol0609356

upstream raw materials:

acryloyl chloride

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

tyrosine

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

Downstream raw materials:

(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

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