N-(tert-butyloxycarbonyl)sarcosine {N-benzyl-N-[4-tert-butyldimethylsilyloxy-(2E)-buten-1-yl]}amide

Base Information

• Chemical Name: N-(tert-butyloxycarbonyl)sarcosine {N-benzyl-N-[4-tert-butyldimethylsilyloxy-(2E)-buten-1-yl]}amide
• CAS No.: 1599423-01-4
• Molecular Formula: C₂₅H₄₂N₂O₄Si
• Molecular Weight: 462.705
• Mol file: 1599423-01-4.mol

Synonyms:N-(tert-butyloxycarbonyl)sarcosine {N-benzyl-N-[4-tert-butyldimethylsilyloxy-(2E)-buten-1-yl]}amide

Chemical Property of N-(tert-butyloxycarbonyl)sarcosine {N-benzyl-N-[4-tert-butyldimethylsilyloxy-(2E)-buten-1-yl]}amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(tert-butyloxycarbonyl)sarcosine {N-benzyl-N-[4-tert-butyldimethylsilyloxy-(2E)-buten-1-yl]}amide

There total 5 articles about N-(tert-butyloxycarbonyl)sarcosine {N-benzyl-N-[4-tert-butyldimethylsilyloxy-(2E)-buten-1-yl]}amide 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: 81.0%

(2E)-N-benzyl-4-(tert-butyldimethylsiloxy)but-2-en-1-amine (1099751-95-7) + N-(tert-butoxycarbonyl)sarcosine (13734-36-6) → N-(tert-butyloxycarbonyl)sarcosine {N-benzyl-N-[4-tert-butyldimethylsilyloxy-(2E)-buten-1-yl]}amide (1599423-01-4)

Guidance literature:

With 2-bromo-1-ethylpyridin-1-ium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -10 ℃; for 0.333333h; Inert atmosphere;

DOI:10.1002/ejoc.201301659

Reference yield:

[(Z)-4-[(tert-butyldimethylsilyl)oxy]-2-buten-1-yl] ethyl carbonate (163976-62-3) → N-(tert-butyloxycarbonyl)sarcosine {N-benzyl-N-[4-tert-butyldimethylsilyloxy-(2E)-buten-1-yl]}amide (1599423-01-4)

Guidance literature:

Multi-step reaction with 3 steps

1: bis(η3-allyl-μ-chloropalladium(II)); sodium hydride; triphenylphosphine / N,N-dimethyl-formamide / Inert atmosphere; Reflux

2: potassium carbonate / methanol; water

3: N-ethyl-N,N-diisopropylamine; 2-bromo-1-ethylpyridin-1-ium tetrafluoroborate / dichloromethane / -10 - 20 °C / Inert atmosphere

With bis(η3-allyl-μ-chloropalladium(II)); 2-bromo-1-ethylpyridin-1-ium tetrafluoroborate; sodium hydride; potassium carbonate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.201301659

Reference yield:

(Z)-4-(tert-butyldimethylsilyloxy)but-2-en-1-ol (91202-69-6,134297-05-5,113123-37-8) → N-(tert-butyloxycarbonyl)sarcosine {N-benzyl-N-[4-tert-butyldimethylsilyloxy-(2E)-buten-1-yl]}amide (1599423-01-4)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / dichloromethane / 0 °C / Inert atmosphere

2: bis(η3-allyl-μ-chloropalladium(II)); sodium hydride; triphenylphosphine / N,N-dimethyl-formamide / Inert atmosphere; Reflux

3: potassium carbonate / methanol; water

4: N-ethyl-N,N-diisopropylamine; 2-bromo-1-ethylpyridin-1-ium tetrafluoroborate / dichloromethane / -10 - 20 °C / Inert atmosphere

With pyridine; bis(η3-allyl-μ-chloropalladium(II)); 2-bromo-1-ethylpyridin-1-ium tetrafluoroborate; sodium hydride; potassium carbonate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.201301659

upstream raw materials:

[(Z)-4-[(tert-butyldimethylsilyl)oxy]-2-buten-1-yl] ethyl carbonate

(2E)-N-benzyl-4-(tert-butyldimethylsiloxy)but-2-en-1-amine

N-(tert-butoxycarbonyl)sarcosine

(Z)-4-(tert-butyldimethylsilyloxy)but-2-en-1-ol

Downstream raw materials:

N-(tert-butyloxycarbonyl)sarcosine {N-benzyl-N-[4-hydroxy-(2E)-buten-1-yl]}amide

N-(tert-butyloxycarbonyl)sarcosine {N-benzyl-N-[4-ethoxycarbonyl-oxy-(2E)-buten-1-yl]}amide

N-(tert-butyloxycarbonyl)sarcosine {N-[4-benzoyloxy-(2E)-buten-1-yl]-N-benzyl}amide

N-(tert-butyloxycarbonyl)-α-deuterio-sarcosine {N-benzyl-N-[4-ethoxy-carbonyloxy-(2E)-buten-1-yl]}amide