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

Base Information

• Chemical Name: 2-amino-2-(3-hydroxy-5-methoxy-phenyl)-N-methyl-acetamide
• CAS No.: 272457-85-9
• Molecular Formula: C₁₀H₁₄N₂O₃
• Molecular Weight: 210.233
• Mol file: 272457-85-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 8 articles about 2-amino-2-(3-hydroxy-5-methoxy-phenyl)-N-methyl-acetamide 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-azido-2-(3-benzyloxy-5-methoxy-phenyl)-N-methyl-acetamide → 2-amino-2-(3-hydroxy-5-methoxy-phenyl)-N-methyl-acetamide (272457-85-9)

Guidance literature:

With hydrogenchloride; hydrogen; palladium on activated charcoal; In ethyl acetate;

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

Reference yield:

methyl 2-(3,5-dihydroxyphenyl)acetate (4724-10-1) → 2-amino-2-(3-hydroxy-5-methoxy-phenyl)-N-methyl-acetamide (272457-85-9)

Guidance literature:

Multi-step reaction with 8 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

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;

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) → 2-amino-2-(3-hydroxy-5-methoxy-phenyl)-N-methyl-acetamide (272457-85-9)

Guidance literature:

Multi-step reaction with 3 steps

1: LiOH / H₂O; tetrahydrofuran / 0 °C

2: EDCl; HOBt / tetrahydrofuran; dimethylformamide

3: H₂; HCl / Pd-C / ethyl acetate

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; N,N-dimethyl-formamide; 1: Hydrolysis / 2: Condensation / 3: Catalytic hydrogenation;

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

upstream raw materials:

methyl 2-(3,5-dihydroxyphenyl)acetate

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

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

(S)-Azido-(3-benzyloxy-5-methoxy-phenyl)-acetic acid

Downstream raw materials:

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

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

Refernces