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

Base Information

• Chemical Name: N-(tert-butyloxycarbonyl)-α-deuterio-sarcosine {N-benzyl-N-[4-ethoxy-carbonyloxy-(2E)-buten-1-yl]}amide
• CAS No.: 1599423-22-9
• Molecular Formula: C₂₂H₃₂N₂O₆
• Molecular Weight: 421.498
• Mol file: 1599423-22-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 8 articles about N-(tert-butyloxycarbonyl)-α-deuterio-sarcosine {N-benzyl-N-[4-ethoxy-carbonyloxy-(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: 90.0%

N-(tert-butyloxycarbonyl)sarcosine {N-benzyl-N-[4-ethoxycarbonyl-oxy-(2E)-buten-1-yl]}amide (1599423-15-0) → N-(tert-butyloxycarbonyl)-α-deuterio-sarcosine {N-benzyl-N-[4-ethoxy-carbonyloxy-(2E)-buten-1-yl]}amide (1599423-22-9)

Guidance literature:

N-(tert-butyloxycarbonyl)sarcosine {N-benzyl-N-[4-ethoxycarbonyl-oxy-(2E)-buten-1-yl]}amide; With n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; toluene; at -78 ℃; for 3h; Inert atmosphere;

With water-d2; In tetrahydrofuran; toluene; at -78 - 20 ℃; Reagent/catalyst; Inert atmosphere;

DOI:10.1002/ejoc.201301659

Reference yield: 90.0%

N-(tert-butyloxycarbonyl)glycine {N-benzyl-N-[4-ethoxycarbonyl-oxy-(2E)-buten-1-yl]}amide (1599423-13-8) → N-(tert-butyloxycarbonyl)-α-deuterio-sarcosine {N-benzyl-N-[4-ethoxy-carbonyloxy-(2E)-buten-1-yl]}amide (1599423-22-9)

Guidance literature:

N-(tert-butyloxycarbonyl)glycine {N-benzyl-N-[4-ethoxycarbonyl-oxy-(2E)-buten-1-yl]}amide; With lithium hexamethyldisilazane; In tetrahydrofuran; toluene; at -78 ℃; for 3h;

With water-d2; In tetrahydrofuran; toluene; at -78 - 20 ℃;

DOI:10.1002/ejoc.201301659

Reference yield:

(2E)-N-benzyl-4-(tert-butyldimethylsiloxy)but-2-en-1-amine (1099751-95-7) → N-(tert-butyloxycarbonyl)-α-deuterio-sarcosine {N-benzyl-N-[4-ethoxy-carbonyloxy-(2E)-buten-1-yl]}amide (1599423-22-9)

Guidance literature:

Multi-step reaction with 4 steps

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

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h

3.1: pyridine / dichloromethane / 0 - 20 °C / Inert atmosphere

4.1: n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane / tetrahydrofuran; toluene / 3 h / -78 °C / Inert atmosphere

4.2: -78 - 20 °C / Inert atmosphere

With pyridine; n-butyllithium; tetrabutyl ammonium fluoride; 2-bromo-1-ethylpyridin-1-ium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1002/ejoc.201301659

upstream raw materials:

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

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

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