(R)-[3-(3-{(S)-[(R)-2-Benzyloxycarbonylamino-3-(4-methoxy-phenyl)-propionylamino]-methylcarbamoyl-methyl}-5-methoxy-phenoxy)-4-methoxy-phenyl]-tert-butoxycarbonylamino-acetic acid

Base Information

• Chemical Name: (R)-[3-(3-{(S)-[(R)-2-Benzyloxycarbonylamino-3-(4-methoxy-phenyl)-propionylamino]-methylcarbamoyl-methyl}-5-methoxy-phenoxy)-4-methoxy-phenyl]-tert-butoxycarbonylamino-acetic acid
• CAS No.: 272457-87-1
• Molecular Formula: C₄₂H₄₈N₄O₁₂
• Molecular Weight: 800.863
• Mol file: 272457-87-1.mol

Synonyms:

Chemical Property of (R)-[3-(3-{(S)-[(R)-2-Benzyloxycarbonylamino-3-(4-methoxy-phenyl)-propionylamino]-methylcarbamoyl-methyl}-5-methoxy-phenoxy)-4-methoxy-phenyl]-tert-butoxycarbonylamino-acetic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-[3-(3-{(S)-[(R)-2-Benzyloxycarbonylamino-3-(4-methoxy-phenyl)-propionylamino]-methylcarbamoyl-methyl}-5-methoxy-phenoxy)-4-methoxy-phenyl]-tert-butoxycarbonylamino-acetic acid

There total 17 articles about (R)-[3-(3-{(S)-[(R)-2-Benzyloxycarbonylamino-3-(4-methoxy-phenyl)-propionylamino]-methylcarbamoyl-methyl}-5-methoxy-phenoxy)-4-methoxy-phenyl]-tert-butoxycarbonylamino-acetic 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:

2-(3-chloro-4-methoxyphenyl)acetic acid (13721-20-5) → (R)-[3-(3-{(S)-[(R)-2-Benzyloxycarbonylamino-3-(4-methoxy-phenyl)-propionylamino]-methylcarbamoyl-methyl}-5-methoxy-phenoxy)-4-methoxy-phenyl]-tert-butoxycarbonylamino-acetic acid (272457-87-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: Et₃N

2.1: tetrahydrofuran / -78 - 20 °C

3.1: KHMDS; Trisyl-N₃ / acetic acid / Heating

4.1: LiOH / tetrahydrofuran; H₂O / 0 °C

5.1: H₂; HCl / Pd-C / ethyl acetate

6.1: NaHCO₃

7.1: 1,2-dichloro-ethane / Heating

7.2: potassium di-t-butylphenoxide; 18-crown-6 / tetrahydrofuran

7.3: acetonitrile / Irradiation

With hydrogenchloride; lithium hydroxide; 2,4,6-Triisopropylbenzenesulfonyl azide; hydrogen; potassium hexamethylsilazane; sodium hydrogencarbonate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; water; acetic acid; ethyl acetate; 1,2-dichloro-ethane; 1.1: Acylation / 2.1: Substitution / 3.1: Evans asymmetric azidation / 4.1: Hydrolysis / 5.1: Catalytic hydrogenation / 6.1: Carbonylation / 7.1: Metallation / 7.2: Etherification / 7.3: Demetallation;

DOI:10.1016/S0040-4039(00)00030-7

Reference yield:

methyl 2-(3,5-dihydroxyphenyl)acetate (4724-10-1) → (R)-[3-(3-{(S)-[(R)-2-Benzyloxycarbonylamino-3-(4-methoxy-phenyl)-propionylamino]-methylcarbamoyl-methyl}-5-methoxy-phenoxy)-4-methoxy-phenyl]-tert-butoxycarbonylamino-acetic acid (272457-87-1)

Guidance literature:

Multi-step reaction with 10 steps

1.1: K₂CO₃; Bu₄NI / acetone / Heating

1.2: K₂CO₃ / acetone / Heating

2.1: 94 percent / KOH / tetrahydrofuran; H₂O / 20 °C

3.1: Et₃N

4.1: tetrahydrofuran / -78 - 20 °C

5.1: KHMDS; Trisyl-N₃ / acetic acid / Heating

6.1: LiOH / H₂O; tetrahydrofuran / 0 °C

7.1: EDCl; HOBt / tetrahydrofuran; dimethylformamide

8.1: H₂; HCl / Pd-C / ethyl acetate

9.1: 81 percent / EDCl; HOBt / tetrahydrofuran; dimethylformamide

10.1: 1,2-dichloro-ethane / Heating

10.2: potassium di-t-butylphenoxide; 18-crown-6 / tetrahydrofuran

10.3: acetonitrile / Irradiation

With hydrogenchloride; potassium hydroxide; lithium hydroxide; 2,4,6-Triisopropylbenzenesulfonyl azide; hydrogen; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; water; acetic acid; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone; 1.1: Etherification / 1.2: Benzylation / 2.1: Hydrolysis / 3.1: Acylation / 4.1: Substitution / 5.1: Evans asymmetric azidation / 6.1: Hydrolysis / 7.1: Condensation / 8.1: Catalytic hydrogenation / 9.1: Condensation / 10.1: Metallation / 10.2: Etherification / 10.3: Demetallation;

DOI:10.1016/S0040-4039(00)00030-7

Reference yield:

(S)-3-[(S)-2-Azido-2-(3-benzyloxy-5-methoxy-phenyl)-acetyl]-4-benzyl-oxazolidin-2-one (185342-01-2) → (R)-[3-(3-{(S)-[(R)-2-Benzyloxycarbonylamino-3-(4-methoxy-phenyl)-propionylamino]-methylcarbamoyl-methyl}-5-methoxy-phenoxy)-4-methoxy-phenyl]-tert-butoxycarbonylamino-acetic acid (272457-87-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: LiOH / H₂O; tetrahydrofuran / 0 °C

2.1: EDCl; HOBt / tetrahydrofuran; dimethylformamide

3.1: H₂; HCl / Pd-C / ethyl acetate

4.1: 81 percent / EDCl; HOBt / tetrahydrofuran; dimethylformamide

5.1: 1,2-dichloro-ethane / Heating

5.2: potassium di-t-butylphenoxide; 18-crown-6 / tetrahydrofuran

5.3: acetonitrile / Irradiation

With hydrogenchloride; lithium hydroxide; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In tetrahydrofuran; water; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 1.1: Hydrolysis / 2.1: Condensation / 3.1: Catalytic hydrogenation / 4.1: Condensation / 5.1: Metallation / 5.2: Etherification / 5.3: Demetallation;

DOI:10.1016/S0040-4039(00)00030-7

upstream raw materials:

2-(3-chloro-4-methoxyphenyl)acetic acid

di-tert-butyl dicarbonate

methyl 2-(3,5-dihydroxyphenyl)acetate

(R)-2-{[(benzyloxy)carbonyl]amino}-3-(4-methoxyphenyl)propionic acid

Refernces