[(R)-1-{[(S)-(3-Hydroxy-5-methoxy-phenyl)-methylcarbamoyl-methyl]-carbamoyl}-2-(4-methoxy-phenyl)-ethyl]-carbamic acid benzyl ester

Base Information

• Chemical Name: [(R)-1-{[(S)-(3-Hydroxy-5-methoxy-phenyl)-methylcarbamoyl-methyl]-carbamoyl}-2-(4-methoxy-phenyl)-ethyl]-carbamic acid benzyl ester
• CAS No.: 272457-86-0
• Molecular Formula: C₂₈H₃₁N₃O₇
• Molecular Weight: 521.57

Synonyms:[(R)-1-{[(S)-(3-Hydroxy-5-methoxy-phenyl)-methylcarbamoyl-methyl]-carbamoyl}-2-(4-methoxy-phenyl)-ethyl]-carbamic acid benzyl ester

Chemical Property of [(R)-1-{[(S)-(3-Hydroxy-5-methoxy-phenyl)-methylcarbamoyl-methyl]-carbamoyl}-2-(4-methoxy-phenyl)-ethyl]-carbamic acid benzyl ester

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Technology Process of [(R)-1-{[(S)-(3-Hydroxy-5-methoxy-phenyl)-methylcarbamoyl-methyl]-carbamoyl}-2-(4-methoxy-phenyl)-ethyl]-carbamic acid benzyl ester

There total 9 articles about [(R)-1-{[(S)-(3-Hydroxy-5-methoxy-phenyl)-methylcarbamoyl-methyl]-carbamoyl}-2-(4-methoxy-phenyl)-ethyl]-carbamic acid benzyl ester 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: 81.0%

(R)-2-{[(benzyloxy)carbonyl]amino}-3-(4-methoxyphenyl)propionic acid (65806-89-5) + 2-amino-2-(3-hydroxy-5-methoxy-phenyl)-N-methyl-acetamide (272457-85-9) → [(R)-1-{[(S)-(3-Hydroxy-5-methoxy-phenyl)-methylcarbamoyl-methyl]-carbamoyl}-2-(4-methoxy-phenyl)-ethyl]-carbamic acid benzyl ester (272457-86-0)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; N,N-dimethyl-formamide;

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

Reference yield:

methyl 2-(3,5-dihydroxyphenyl)acetate (4724-10-1) → [(R)-1-{[(S)-(3-Hydroxy-5-methoxy-phenyl)-methylcarbamoyl-methyl]-carbamoyl}-2-(4-methoxy-phenyl)-ethyl]-carbamic acid benzyl ester (272457-86-0)

Guidance literature:

Multi-step reaction with 9 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

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; 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;

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

Reference yield:

(S)-4-Benzyl-3-[2-(3-benzyloxy-5-methoxy-phenyl)-acetyl]-oxazolidin-2-one (185342-16-9) → [(R)-1-{[(S)-(3-Hydroxy-5-methoxy-phenyl)-methylcarbamoyl-methyl]-carbamoyl}-2-(4-methoxy-phenyl)-ethyl]-carbamic acid benzyl ester (272457-86-0)

Guidance literature:

Multi-step reaction with 5 steps

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

2: LiOH / H₂O; tetrahydrofuran / 0 °C

3: EDCl; HOBt / tetrahydrofuran; dimethylformamide

4: H₂; HCl / Pd-C / ethyl acetate

5: 81 percent / EDCl; HOBt / tetrahydrofuran; dimethylformamide

With hydrogenchloride; lithium hydroxide; 2,4,6-Triisopropylbenzenesulfonyl azide; hydrogen; potassium hexamethylsilazane; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In tetrahydrofuran; water; acetic acid; ethyl acetate; N,N-dimethyl-formamide; 1: Evans asymmetric azidation / 2: Hydrolysis / 3: Condensation / 4: Catalytic hydrogenation / 5: Condensation;

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

upstream raw materials:

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

2-amino-2-(3-hydroxy-5-methoxy-phenyl)-N-methyl-acetamide

methyl 2-(3,5-dihydroxyphenyl)acetate

(S)-4-Benzyl-3-[2-(3-benzyloxy-5-methoxy-phenyl)-acetyl]-oxazolidin-2-one

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