(1S)-tert-butyl-1-{[(2,4-dimethoxybenzyl)amino]methyl}but-3-enylcarbamate

Base Information

• Chemical Name: (1S)-tert-butyl-1-{[(2,4-dimethoxybenzyl)amino]methyl}but-3-enylcarbamate
• CAS No.: 335160-61-7
• Molecular Formula: C₁₉H₃₀N₂O₄
• Molecular Weight: 350.458
• Mol file: 335160-61-7.mol

Synonyms:(1S)-tert-butyl-1-{[(2,4-dimethoxybenzyl)amino]methyl}but-3-enylcarbamate

Chemical Property of (1S)-tert-butyl-1-{[(2,4-dimethoxybenzyl)amino]methyl}but-3-enylcarbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S)-tert-butyl-1-{[(2,4-dimethoxybenzyl)amino]methyl}but-3-enylcarbamate

There total 3 articles about (1S)-tert-butyl-1-{[(2,4-dimethoxybenzyl)amino]methyl}but-3-enylcarbamate 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%

2,4-dimethoxybenzylamine hydrochloride (20781-21-9) + tert-butyl (S)-(1-oxopent-4-en-2-yl)carbamate (95107-99-6) → (1S)-tert-butyl-1-{[(2,4-dimethoxybenzyl)amino]methyl}but-3-enylcarbamate (335160-61-7)

Guidance literature:

With 4 A molecular sieve; sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; at 20 ℃; for 14h;

DOI:10.1021/ol015504w

Reference yield:

(2S)-2-[(tert-butoxycarbonyl)amino]pent-4-enoic acid (90600-20-7) → (1S)-tert-butyl-1-{[(2,4-dimethoxybenzyl)amino]methyl}but-3-enylcarbamate (335160-61-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 67 percent / EDC; HOBt / dimethylformamide / 24 h / 0 °C

2: 85 percent / LiAlH₄ / diethyl ether / 3 h / -50 - 5 °C

3: 90 percent / Na(AcO)3BH; 4 Angstroem molecular sieves / 1,2-dichloro-ethane / 14 h / 20 °C

With lithium aluminium tetrahydride; 4 A molecular sieve; sodium tris(acetoxy)borohydride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In diethyl ether; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1021/ol015504w

Reference yield:

(S)-2-[N2-[(tert-butyloxy)carbonyl]amino]-N-methoxy-N-methyl-4-penteneamide (208521-14-6) → (1S)-tert-butyl-1-{[(2,4-dimethoxybenzyl)amino]methyl}but-3-enylcarbamate (335160-61-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / LiAlH₄ / diethyl ether / 3 h / -50 - 5 °C

2: 90 percent / Na(AcO)3BH; 4 Angstroem molecular sieves / 1,2-dichloro-ethane / 14 h / 20 °C

With lithium aluminium tetrahydride; 4 A molecular sieve; sodium tris(acetoxy)borohydride; In diethyl ether; 1,2-dichloro-ethane;

DOI:10.1021/ol015504w

upstream raw materials:

2,4-dimethoxybenzylamine hydrochloride

tert-butyl (S)-(1-oxopent-4-en-2-yl)carbamate

(2S)-2-[(tert-butoxycarbonyl)amino]pent-4-enoic acid

(S)-2-[N²-[(tert-butyloxy)carbonyl]amino]-N-methoxy-N-methyl-4-penteneamide

Downstream raw materials:

5(S),3(S)-3-benzyl-4-tert-butoxycarbonyl-1-(2,4-dimethoxybenzyl)-5-[2-(phenylsulfonyloxy)ethyl]-2-piperazinone

1(R),5(S)-8-[1-(4-cyano-3-fluorobenzyl)-5-imidazolylmethyl]-3-(2,4-dimethoxybenzyl)-3,8-diaza-2-oxobicyclo[3.2.1]octane

(S)-4-tert-butoxycarbonyl-1-(2,4-dimethoxybenzyl)-5-[2-(phenylsulfonyloxy)ethyl]-2-piperazinone

5(S),3(S)-3-benzyl-4-tert-butoxycarbonyl-1-(2,4-dimethoxybenzyl)-5-(2-hydroxyethyl)-2-piperazinone