(2S,3R)-N-(4-methoxybenzyl)-N-(t-butoxycarbonylmethyl)-2-bromo-3-hydroxybutyramide

Base Information

• Chemical Name: (2S,3R)-N-(4-methoxybenzyl)-N-(t-butoxycarbonylmethyl)-2-bromo-3-hydroxybutyramide
• CAS No.: 98076-57-4
• Molecular Formula: C₁₈H₂₆BrNO₅
• Molecular Weight: 416.312
• Mol file: 98076-57-4.mol

Synonyms:(2S,3R)-N-(4-methoxybenzyl)-N-(t-butoxycarbonylmethyl)-2-bromo-3-hydroxybutyramide

Chemical Property of (2S,3R)-N-(4-methoxybenzyl)-N-(t-butoxycarbonylmethyl)-2-bromo-3-hydroxybutyramide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-N-(4-methoxybenzyl)-N-(t-butoxycarbonylmethyl)-2-bromo-3-hydroxybutyramide

There total 1 articles about (2S,3R)-N-(4-methoxybenzyl)-N-(t-butoxycarbonylmethyl)-2-bromo-3-hydroxybutyramide 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: 71.5%

(2S,3R)-2-Bromo-3-hydroxybutanoic acid (70702-03-3) + [(4-Methoxy-benzyl)-amino]-acetic Acid Tert-butyl Ester (98076-56-3) → (2S,3R)-N-(4-methoxybenzyl)-N-(t-butoxycarbonylmethyl)-2-bromo-3-hydroxybutyramide (98076-57-4)

Guidance literature:

With dicyclohexyl-carbodiimide; In tetrahydrofuran; at 20 - 30 ℃; for 0.5h;

DOI:10.1246/bcsj.58.3264

Reference yield:

(2S,3R)-N-(4-methoxybenzyl)-N-(t-butoxycarbonylmethyl)-2-bromo-3-hydroxybutyramide (98076-57-4) → (3S,4R)-3-<(R)-1-(t-butyldimethylsiloxy)ethyl>-1-(4-methoxybenzyl)-4-<(phenylthiocarbonyl)methyl>-2-azetidinone (102679-25-4)

Guidance literature:

Multi-step reaction with 6 steps

1: n-BuLi, hexamethyldisilazane / tetrahydrofuran; hexane / 1) 1) 2 to 3 deg C, 2) 20 to 23 deg C, 30 min

2: 5percent NaHCO₃ / ethyl acetate

3: 1) 4-dimethylaminopyridine, 2) 1 M NaOH / 1) DMF, r.t., 16 h, 2) EtOH, 60 to 70 deg C, 2 h

4: 2) CuI / 1) THF, DMF, 0 deg C, 2) Et₂O, 0 deg C, 5 min; THF, -78 deg C, 15 min

5: 86 percent / m-chloroperbenzoic acid / CHCl₃ / Ambient temperature

6: trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / Ambient temperature

With dmap; sodium hydroxide; copper(l) iodide; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; hexane; dichloromethane; chloroform; ethyl acetate;

DOI:10.1246/bcsj.58.3264

Reference yield:

(2S,3R)-N-(4-methoxybenzyl)-N-(t-butoxycarbonylmethyl)-2-bromo-3-hydroxybutyramide (98076-57-4) → (3S,4R)-1-(4-methoxybenzyl)-4-<(phenylthiocarbonyl)methyl>-3-<(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-2-azetidinone (90629-24-6)

Guidance literature:

Multi-step reaction with 6 steps

1: n-BuLi, hexamethyldisilazane / tetrahydrofuran; hexane / 1) 1) 2 to 3 deg C, 2) 20 to 23 deg C, 30 min

2: 5percent NaHCO₃ / ethyl acetate

3: trifluoroacetic acid / 3 h / 0 °C

4: 51.3 percent / dimethylformamide; acetic acid / 0.25 h / 50 - 55 °C

5: 74 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 1 h

6: 94.9 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / Ambient temperature

With dmap; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; sodium hydrogencarbonate; 1,1,1,3,3,3-hexamethyl-disilazane; trifluoroacetic acid; In tetrahydrofuran; hexane; dichloromethane; acetic acid; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1246/bcsj.58.3264

upstream raw materials:

(2S,3R)-2-Bromo-3-hydroxybutanoic acid

[(4-Methoxy-benzyl)-amino]-acetic Acid Tert-butyl Ester

Downstream raw materials:

3(S)-<1(R)-<(tert-butyldimethylsilyl)oxy>ethyl>-4(R)-<<(phenylthio)carbonyl>methyl>azetidin-2-one

(2S,3S)-3-<(R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-1-<(4-methoxyphenyl)methyl>-4-oxo-2-azetidinecarboxylic acid

(3S,4R)-3-<(R)-1-(t-butyldimethylsiloxy)ethyl>-1-(4-methoxybenzyl)-4-<(phenylthiocarbonyl)methyl>-2-azetidinone

(3S,4R)-1-(4-methoxybenzyl)-4-<(phenylthiocarbonyl)methyl>-3-<(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-2-azetidinone