tert-butyl 2-(benzylamino)-2-(4-fluorobenzyl)-3-hydroxypropanoate

Base Information

• Chemical Name: tert-butyl 2-(benzylamino)-2-(4-fluorobenzyl)-3-hydroxypropanoate
• CAS No.: 1613450-06-8
• Molecular Formula: C₂₁H₂₆FNO₃
• Molecular Weight: 359.441
• Mol file: 1613450-06-8.mol

Synonyms:tert-butyl 2-(benzylamino)-2-(4-fluorobenzyl)-3-hydroxypropanoate

Chemical Property of tert-butyl 2-(benzylamino)-2-(4-fluorobenzyl)-3-hydroxypropanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl 2-(benzylamino)-2-(4-fluorobenzyl)-3-hydroxypropanoate

There total 6 articles about tert-butyl 2-(benzylamino)-2-(4-fluorobenzyl)-3-hydroxypropanoate 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: 98.0%

4-(4-fluorobenzyl)-2-phenyl-1,3-oxazoline-4-carboxylic acid tert-butyl ester → tert-butyl 2-(benzylamino)-2-(4-fluorobenzyl)-3-hydroxypropanoate (1613450-06-8)

Guidance literature:

With sodium cyanoborohydride; In acetic acid; at 0 - 20 ℃; for 16h; regioselective reaction;

DOI:10.1016/j.tet.2014.05.004

Reference yield:

ethyl benzimidate hydrochloride (5333-86-8) → tert-butyl 2-(benzylamino)-2-(4-fluorobenzyl)-3-hydroxypropanoate (1613450-06-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium carbonate / dichloromethane; water

1.2: 2 h / Reflux

2.1: sodium hydroxide / water; methanol; acetone / 3.33 h / 2 °C / Cooling with ice

3.1: hydrogenchloride / water / 1 h / 0 °C / pH < 3

4.1: dmap / dichloromethane; tert-butyl alcohol / 1 h / Inert atmosphere; Reflux

5.1: tetrabutylammomium bromide; potassium hydroxide / dichloromethane; toluene / 0 - 20 °C / Inert atmosphere

6.1: sodium cyanoborohydride / acetic acid / 16 h / 0 - 20 °C

With hydrogenchloride; dmap; tetrabutylammomium bromide; sodium cyanoborohydride; sodium carbonate; potassium hydroxide; sodium hydroxide; In methanol; dichloromethane; water; acetic acid; acetone; toluene; tert-butyl alcohol;

DOI:10.1016/j.tet.2014.05.004

Reference yield:

benzonitrile (100-47-0) → tert-butyl 2-(benzylamino)-2-(4-fluorobenzyl)-3-hydroxypropanoate (1613450-06-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: acetyl chloride / diethyl ether / 0.75 h / 0 °C / Inert atmosphere

1.2: 730.5 h / 2 °C / Inert atmosphere

2.1: sodium carbonate / dichloromethane; water

2.2: 2 h / Reflux

3.1: sodium hydroxide / water; methanol; acetone / 3.33 h / 2 °C / Cooling with ice

4.1: hydrogenchloride / water / 1 h / 0 °C / pH < 3

5.1: dmap / dichloromethane; tert-butyl alcohol / 1 h / Inert atmosphere; Reflux

6.1: tetrabutylammomium bromide; potassium hydroxide / dichloromethane; toluene / 0 - 20 °C / Inert atmosphere

7.1: sodium cyanoborohydride / acetic acid / 16 h / 0 - 20 °C

With hydrogenchloride; dmap; tetrabutylammomium bromide; sodium cyanoborohydride; sodium carbonate; acetyl chloride; potassium hydroxide; sodium hydroxide; In methanol; diethyl ether; dichloromethane; water; acetic acid; acetone; toluene; tert-butyl alcohol; 1.1: |Pinner Amidine Synthesis / 1.2: |Pinner Imino Ether Synthesis;

DOI:10.1016/j.tet.2014.05.004

upstream raw materials:

ethyl benzimidate hydrochloride

methyl 2-phenyl-2-oxazoline-4-carboxylate

benzonitrile

sodium 2-phenyloxazoline-4-carboxylate

Downstream raw materials:

tert-butyl 3-benzyl-4-(4-fluorobenzyl)-2-oxo-1,2,3-oxathiazolidine-4-carboxylate

tert-butyl 3-benzyl-4-(4-fluorobenzyl)-2,2-dioxo-1,2,3-oxathiazolidine-4-carboxylate

tert-butyl 2-benzylamino-3-((R)-2-(tert-butoxycarbonylamino)-3-methoxy-3-oxopropylthio)-2-(4-fluorobenzyl)propanoate

Refernces