3'-N-demethyl-4-O-(2-diethylaminoethanoyl)-2'-O-3'-N-di-{[(phenylmethyl)oxy]carbonyl}-6-O-methyl-9a-aza-9a-homoerythromycin A

Base Information

• Chemical Name: 3'-N-demethyl-4-O-(2-diethylaminoethanoyl)-2'-O-3'-N-di-{[(phenylmethyl)oxy]carbonyl}-6-O-methyl-9a-aza-9a-homoerythromycin A
• CAS No.: 1236808-99-3
• Molecular Formula: C₅₉H₉₁N₃O₁₈
• Molecular Weight: 1130.38
• Mol file: 1236808-99-3.mol

Synonyms:3'-N-demethyl-4-O-(2-diethylaminoethanoyl)-2'-O-3'-N-di-{[(phenylmethyl)oxy]carbonyl}-6-O-methyl-9a-aza-9a-homoerythromycin A

Chemical Property of 3'-N-demethyl-4-O-(2-diethylaminoethanoyl)-2'-O-3'-N-di-{[(phenylmethyl)oxy]carbonyl}-6-O-methyl-9a-aza-9a-homoerythromycin A

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3'-N-demethyl-4-O-(2-diethylaminoethanoyl)-2'-O-3'-N-di-{[(phenylmethyl)oxy]carbonyl}-6-O-methyl-9a-aza-9a-homoerythromycin A

There total 3 articles about 3'-N-demethyl-4-O-(2-diethylaminoethanoyl)-2'-O-3'-N-di-{[(phenylmethyl)oxy]carbonyl}-6-O-methyl-9a-aza-9a-homoerythromycin A 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: 63.0%

2-(diethylamino)acetic acid (1606-01-5) + 3'-N-demethyl-2'-O-3'-N-di-{[(phenylmethyl)oxy]carbonyl}-6-O-methyl-9a-aza-9a-homoerythromycin A (1236808-96-0) → 3'-N-demethyl-4-O-(2-diethylaminoethanoyl)-2'-O-3'-N-di-{[(phenylmethyl)oxy]carbonyl}-6-O-methyl-9a-aza-9a-homoerythromycin A (1236808-99-3)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 2 - 20 ℃; Product distribution / selectivity; Industry scale;

Reference yield:

6-methoxyerythromycin A 9-oxime (127253-06-9) → 3'-N-demethyl-4-O-(2-diethylaminoethanoyl)-2'-O-3'-N-di-{[(phenylmethyl)oxy]carbonyl}-6-O-methyl-9a-aza-9a-homoerythromycin A (1236808-99-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Toluene-2-sulfonyl chloride / acetone / 0.33 h / -10 - -8 °C / Industry scale

1.2: 0 - 20 °C

1.3: 70 °C

2.1: sodium hydrogencarbonate / 1,4-dioxane / 30 - 60 °C / Industry scale

3.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 2 - 20 °C / Industry scale

With dmap; sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; Toluene-2-sulfonyl chloride; In 1,4-dioxane; dichloromethane; acetone;

Reference yield:

6-O-methyl-9a-aza-9a-homoerythromycin A (210912-02-0) + benzyl chloroformate (501-53-1,94274-21-2) → 3'-N-demethyl-4-O-(2-diethylaminoethanoyl)-2'-O-3'-N-di-{[(phenylmethyl)oxy]carbonyl}-6-O-methyl-9a-aza-9a-homoerythromycin A (1236808-99-3)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydrogencarbonate / 1,4-dioxane / 30 - 60 °C / Industry scale

2: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 2 - 20 °C / Industry scale

With dmap; sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In 1,4-dioxane; dichloromethane;

upstream raw materials:

2-(diethylamino)acetic acid

3'-N-demethyl-2'-O-3'-N-di-{[(phenylmethyl)oxy]carbonyl}-6-O-methyl-9a-aza-9a-homoerythromycin A

6-O-methyl-9a-aza-9a-homoerythromycin A

benzyl chloroformate