(3S,3S')-3--3-(4-methoxyphenyl)-1-(2,2,2-trichloroethoxycarbonyloxy)propane

Base Information

• Chemical Name: (3S,3S')-3--3-(4-methoxyphenyl)-1-(2,2,2-trichloroethoxycarbonyloxy)propane
• CAS No.: 159848-97-2
• Molecular Formula: C₃₃H₄₅Cl₃N₂O₉
• Molecular Weight: 720.087
• Mol file: 159848-97-2.mol

Synonyms:

Chemical Property of (3S,3S')-3--3-(4-methoxyphenyl)-1-(2,2,2-trichloroethoxycarbonyloxy)propane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,3S')-3--3-(4-methoxyphenyl)-1-(2,2,2-trichloroethoxycarbonyloxy)propane

There total 12 articles about (3S,3S')-3--3-(4-methoxyphenyl)-1-(2,2,2-trichloroethoxycarbonyloxy)propane 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%

(3S,3S')-3--3-(4-methoxyphenyl)-1-propanol (159848-96-1) + 2,2,2-Trichloroethyl chloroformate (17341-93-4) → (3S,3S')-3--3-(4-methoxyphenyl)-1-(2,2,2-trichloroethoxycarbonyloxy)propane (159848-97-2)

Guidance literature:

With pyridine; dmap; 0 deg C 1 h then rt., 1 h;

DOI:10.1016/S0040-4020(01)85520-4

Reference yield:

(S)-β-amino-β-(4-methoxyphenyl)propionic acid (131690-56-7) → (3S,3S')-3--3-(4-methoxyphenyl)-1-(2,2,2-trichloroethoxycarbonyloxy)propane (159848-97-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 4.75 percent / 1N NaOH / tetrahydrofuran / 4 h / Ambient temperature

2: 1.20 g / K₂CO₃ / dimethylformamide / 11 h / Ambient temperature

3: 94 percent / 10percent HCl / methanol / 1 h / Ambient temperature

4: 86 percent / 1M NaBH₃CN / methanol; acetic acid; tetrahydrofuran / 15 h / 0 - 14 °C

5: 94 percent / dioxane / 14 h / Ambient temperature

6: 97 percent / 2M LiBH₄ / diethyl ether; tetrahydrofuran / 13 h / Ambient temperature

7: 98 percent / DMAP, pyridine / 0 deg C 1 h then rt., 1 h

With pyridine; hydrogenchloride; dmap; sodium hydroxide; lithium borohydride; sodium cyanoborohydride; potassium carbonate; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; acetic acid; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)85520-4

Reference yield:

methyl (+)-(3S)-3-amino-3-(4-methoxyphenyl)propanoate (159848-76-7,227319-36-0) → (3S,3S')-3--3-(4-methoxyphenyl)-1-(2,2,2-trichloroethoxycarbonyloxy)propane (159848-97-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 86 percent / 1M NaBH₃CN / methanol; acetic acid; tetrahydrofuran / 15 h / 0 - 14 °C

2: 94 percent / dioxane / 14 h / Ambient temperature

3: 97 percent / 2M LiBH₄ / diethyl ether; tetrahydrofuran / 13 h / Ambient temperature

4: 98 percent / DMAP, pyridine / 0 deg C 1 h then rt., 1 h

With pyridine; dmap; lithium borohydride; sodium cyanoborohydride; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; acetic acid;

DOI:10.1016/S0040-4020(01)85520-4

upstream raw materials:

(3S,3S')-3--3-(4-methoxyphenyl)-1-propanol

2,2,2-Trichloroethyl chloroformate

(S)-β-amino-β-(4-methoxyphenyl)propionic acid

methyl (+)-(3S)-3-amino-3-(4-methoxyphenyl)propanoate

Downstream raw materials:

(2S:3'S:3''S)-N-[N-(3-amino-3-carboxypropyl)-3-amino-3-carboxypropyl]-azetidine-2-carboxylic acid