Toluene-4-sulfonic acid (S)-2-benzyloxycarbonylamino-3-(4-methoxy-phenyl)-propyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (S)-2-benzyloxycarbonylamino-3-(4-methoxy-phenyl)-propyl ester
• CAS No.: 115424-06-1
• Molecular Formula: C₂₅H₂₇NO₆S
• Molecular Weight: 469.558
• Mol file: 115424-06-1.mol

Synonyms:Toluene-4-sulfonic acid (S)-2-benzyloxycarbonylamino-3-(4-methoxy-phenyl)-propyl ester

Chemical Property of Toluene-4-sulfonic acid (S)-2-benzyloxycarbonylamino-3-(4-methoxy-phenyl)-propyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Toluene-4-sulfonic acid (S)-2-benzyloxycarbonylamino-3-(4-methoxy-phenyl)-propyl ester

There total 8 articles about Toluene-4-sulfonic acid (S)-2-benzyloxycarbonylamino-3-(4-methoxy-phenyl)-propyl ester 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: 83.6%

(S)-benzyl (1-hydroxy-3-(4-methoxyphenyl)propan-2-yl)carbamate (115424-05-0) + p-toluenesulfonyl chloride (98-59-9) → Toluene-4-sulfonic acid (S)-2-benzyloxycarbonylamino-3-(4-methoxy-phenyl)-propyl ester (115424-06-1)

Guidance literature:

With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide; In water; toluene; at 15 - 20 ℃; for 0.75h; Cooling with ice;

DOI:10.1080/00397911.2012.748075

Reference yield:

N-benzyloxycarbonylamino-3-(4-methoxyphenyl)propionic acid ethyl ester (115424-04-9) → Toluene-4-sulfonic acid (S)-2-benzyloxycarbonylamino-3-(4-methoxy-phenyl)-propyl ester (115424-06-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / NaBH₄ / ethanol / 7 h / Ambient temperature

2: 341 g / aq. NaOH, n-Bu₄NHSO₄ / benzene; H₂O / 0.5 h / 15 - 20 °C

With sodium hydroxide; sodium tetrahydroborate; tetra(n-butyl)ammonium hydrogensulfate; In ethanol; water; benzene;

DOI:10.1080/00397919808007167

Reference yield:

L-tyrosine ethyl ester (949-67-7) → Toluene-4-sulfonic acid (S)-2-benzyloxycarbonylamino-3-(4-methoxy-phenyl)-propyl ester (115424-06-1)

Guidance literature:

Multi-step reaction with 4 steps

1: K₂CO₃ / ethyl acetate; H₂O / 0.5 h / 3 - 8 °C

2: K₂CO₃ / dimethylsulfoxide / 16 h / Ambient temperature

3: 86 percent / NaBH₄ / ethanol / 7 h / Ambient temperature

4: 341 g / aq. NaOH, n-Bu₄NHSO₄ / benzene; H₂O / 0.5 h / 15 - 20 °C

With sodium hydroxide; sodium tetrahydroborate; tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate; In ethanol; water; dimethyl sulfoxide; ethyl acetate; benzene;

DOI:10.1080/00397919808007167

upstream raw materials:

(S)-benzyl (1-hydroxy-3-(4-methoxyphenyl)propan-2-yl)carbamate

p-toluenesulfonyl chloride

L-tyrosine ethyl ester

N-[(phenylmethoxy)carbonyl]-L-tyrosine

Downstream raw materials:

l-para-Methoxyamphetamine hydrochloride

O-benzyl carbamate

Estragole

[(S)-1-Iodomethyl-2-(4-methoxy-phenyl)-ethyl]-carbamic acid benzyl ester