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

Base Information

• Chemical Name: allyl (2S)-2-({3-[(N-acryloyl-3-chloro-O-methyl-D-tyrosyl)amino]-2,2-dimethylpropanoyl}oxy)-4-methylpentanoate
• CAS No.: 905309-67-3
• Molecular Formula: C₂₇H₃₇ClN₂O₇
• Molecular Weight: 537.053
• Mol file: 905309-67-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 13 articles about allyl (2S)-2-({3-[(N-acryloyl-3-chloro-O-methyl-D-tyrosyl)amino]-2,2-dimethylpropanoyl}oxy)-4-methylpentanoate 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: 78.0%

allyl (2S)-2-[(3-amino-2,2-dimethylpropanoyl)oxy]-4-methylpentanoate (905309-55-9) + (2R)-2-(acryloylamino)-3-(3-chloro-4-methoxyphenyl)propanoic acid (905309-58-2) → allyl (2S)-2-({3-[(N-acryloyl-3-chloro-O-methyl-D-tyrosyl)amino]-2,2-dimethylpropanoyl}oxy)-4-methylpentanoate (905309-67-3)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1021/ol0609356

Reference yield:

methyl (2R)-2-(acryloylamino)-3-(3-chloro-4-methoxyphenyl)propanoate (905309-57-1) → allyl (2S)-2-({3-[(N-acryloyl-3-chloro-O-methyl-D-tyrosyl)amino]-2,2-dimethylpropanoyl}oxy)-4-methylpentanoate (905309-67-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / LiOH / tetrahydrofuran; methanol; H₂O / 4 h / 20 °C

2: 78 percent / HOBt; DIEA; EDCI / CH₂Cl₂ / 16 h / 20 °C

With lithium hydroxide; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1021/ol0609356

Reference yield:

L-leucine (61-90-5,21675-61-6,25248-98-0,70-45-1) → allyl (2S)-2-({3-[(N-acryloyl-3-chloro-O-methyl-D-tyrosyl)amino]-2,2-dimethylpropanoyl}oxy)-4-methylpentanoate (905309-67-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 88 percent / NaNO₂; H₂SO₄ / H₂O / 5 h / 0 - 20 °C

2: 94 percent / Na₂CO₃; tetrabutylammonium chloride / H₂O; CH₂Cl₂ / 16 h / 20 °C

3: 93 percent / EDCI; DMAP / CH₂Cl₂ / 16 h / 20 °C

4: 97 percent / TFA / CH₂Cl₂ / 3 h / 20 °C

5: 78 percent / HOBt; DIEA; EDCI / CH₂Cl₂ / 16 h / 20 °C

With dmap; sulfuric acid; tetrabutyl-ammonium chloride; sodium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; sodium nitrite; In dichloromethane; water;

DOI:10.1021/ol0609356

upstream raw materials:

allyl (2S)-2-[(3-amino-2,2-dimethylpropanoyl)oxy]-4-methylpentanoate

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

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

L-leucine

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

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

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

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