methyl (3S,3S')-3-<3'-tert-butoxycarbonylamino-3'-(4-methoxyphenyl)propylamino>-3-(4-methoxyphenyl)propionate

Base Information

• Chemical Name: methyl (3S,3S')-3-<3'-tert-butoxycarbonylamino-3'-(4-methoxyphenyl)propylamino>-3-(4-methoxyphenyl)propionate
• CAS No.: 159848-94-9
• Molecular Formula: C₂₆H₃₆N₂O₆
• Molecular Weight: 472.582
• Mol file: 159848-94-9.mol

Synonyms:methyl (3S,3S')-3-<3'-tert-butoxycarbonylamino-3'-(4-methoxyphenyl)propylamino>-3-(4-methoxyphenyl)propionate

Chemical Property of methyl (3S,3S')-3-<3'-tert-butoxycarbonylamino-3'-(4-methoxyphenyl)propylamino>-3-(4-methoxyphenyl)propionate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (3S,3S')-3-<3'-tert-butoxycarbonylamino-3'-(4-methoxyphenyl)propylamino>-3-(4-methoxyphenyl)propionate

There total 8 articles about methyl (3S,3S')-3-<3'-tert-butoxycarbonylamino-3'-(4-methoxyphenyl)propylamino>-3-(4-methoxyphenyl)propionate 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: 86.0%

methyl (+)-(3S)-3-amino-3-(4-methoxyphenyl)propanoate (159848-76-7,227319-36-0) + (S)-3-tert-butoxycarbonylamino-3-(4-methoxyphenyl)-1-oxopropane (159848-93-8) → methyl (3S,3S')-3-<3'-tert-butoxycarbonylamino-3'-(4-methoxyphenyl)propylamino>-3-(4-methoxyphenyl)propionate (159848-94-9)

Guidance literature:

With sodium cyanoborohydride; In tetrahydrofuran; methanol; acetic acid; at 0 - 14 ℃; for 15h;

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

Reference yield:

(S)-β-amino-β-(4-methoxyphenyl)propionic acid (131690-56-7) → methyl (3S,3S')-3-<3'-tert-butoxycarbonylamino-3'-(4-methoxyphenyl)propylamino>-3-(4-methoxyphenyl)propionate (159848-94-9)

Guidance literature:

Multi-step reaction with 4 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

With hydrogenchloride; sodium hydroxide; sodium cyanoborohydride; potassium carbonate; In tetrahydrofuran; methanol; acetic acid; N,N-dimethyl-formamide;

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

Reference yield:

1,1-dimethylethyl (R)-N-[2-hydroxy-1-(4-methoxyphenyl)-ethyl]carbamate (159848-74-5) → methyl (3S,3S')-3-<3'-tert-butoxycarbonylamino-3'-(4-methoxyphenyl)propylamino>-3-(4-methoxyphenyl)propionate (159848-94-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 94 percent / pyridine / 2 h / 0 °C

2: 83 percent / 18-crown-6 / dimethylsulfoxide / 3 h / 50 °C

3: 3.7 g / conc. HCl / tetrahydrofuran / 12 h / 100 °C

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

5: 1.20 g / K₂CO₃ / dimethylformamide / 11 h / Ambient temperature

6: 94 percent / 10percent HCl / methanol / 1 h / Ambient temperature

7: 86 percent / 1M NaBH₃CN / methanol; acetic acid; tetrahydrofuran / 15 h / 0 - 14 °C

With pyridine; hydrogenchloride; sodium hydroxide; 18-crown-6 ether; sodium cyanoborohydride; potassium carbonate; In tetrahydrofuran; methanol; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide;

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

upstream raw materials:

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

(S)-3-tert-butoxycarbonylamino-3-(4-methoxyphenyl)-1-oxopropane

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

1,1-dimethylethyl (R)-N-[2-hydroxy-1-(4-methoxyphenyl)-ethyl]carbamate

Downstream raw materials:

methyl (3S,3S')-3--3-(4-methoxyphenyl)propionate

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

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

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