(S)-3-[4-(tert-butyldimethylsilyloxy)phenyl]-2-(N,N-dimethylamino)-N-methoxy-N-methylpropanamide

Base Information

• Chemical Name: (S)-3-[4-(tert-butyldimethylsilyloxy)phenyl]-2-(N,N-dimethylamino)-N-methoxy-N-methylpropanamide
• CAS No.: 1260499-44-2
• Molecular Formula: C₁₉H₃₄N₂O₃Si
• Molecular Weight: 366.576
• Mol file: 1260499-44-2.mol

Synonyms:(S)-3-[4-(tert-butyldimethylsilyloxy)phenyl]-2-(N,N-dimethylamino)-N-methoxy-N-methylpropanamide

Chemical Property of (S)-3-[4-(tert-butyldimethylsilyloxy)phenyl]-2-(N,N-dimethylamino)-N-methoxy-N-methylpropanamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-[4-(tert-butyldimethylsilyloxy)phenyl]-2-(N,N-dimethylamino)-N-methoxy-N-methylpropanamide

There total 4 articles about (S)-3-[4-(tert-butyldimethylsilyloxy)phenyl]-2-(N,N-dimethylamino)-N-methoxy-N-methylpropanamide 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: 92.0%

methyl (S)-N,N-dimethyl-O-(tert-butyldimethylsilyl)tyrosinate (1260499-43-1) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → (S)-3-[4-(tert-butyldimethylsilyloxy)phenyl]-2-(N,N-dimethylamino)-N-methoxy-N-methylpropanamide (1260499-44-2)

Guidance literature:

With isopropylmagnesium bromide; In tetrahydrofuran; at -20 ℃; for 1h;

DOI:10.1271/bbb.100361

Reference yield:

L-tyrosine (60-18-4,18875-48-4,25619-78-7,30704-25-7) → (S)-3-[4-(tert-butyldimethylsilyloxy)phenyl]-2-(N,N-dimethylamino)-N-methoxy-N-methylpropanamide (1260499-44-2)

Guidance literature:

Multi-step reaction with 4 steps

1: thionyl chloride / 4 h / 0 °C / Reflux

2: palladium 10% on activated carbon; hydrogen / methanol; water / 3 h

3: 1H-imidazole / N,N-dimethyl-formamide / 18 h / 0 °C

4: isopropylmagnesium bromide / tetrahydrofuran / 1 h / -20 °C

With 1H-imidazole; thionyl chloride; palladium 10% on activated carbon; hydrogen; isopropylmagnesium bromide; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide;

DOI:10.1271/bbb.100361

Reference yield:

L-Tyr-OMe (1080-06-4) → (S)-3-[4-(tert-butyldimethylsilyloxy)phenyl]-2-(N,N-dimethylamino)-N-methoxy-N-methylpropanamide (1260499-44-2)

Guidance literature:

Multi-step reaction with 3 steps

1: palladium 10% on activated carbon; hydrogen / methanol; water / 3 h

2: 1H-imidazole / N,N-dimethyl-formamide / 18 h / 0 °C

3: isopropylmagnesium bromide / tetrahydrofuran / 1 h / -20 °C

With 1H-imidazole; palladium 10% on activated carbon; hydrogen; isopropylmagnesium bromide; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide;

DOI:10.1271/bbb.100361

upstream raw materials:

methyl (S)-N,N-dimethyl-O-(tert-butyldimethylsilyl)tyrosinate

N,O-dimethylhydroxylamine*hydrochloride

L-Tyr-OMe

L-tyrosine

Downstream raw materials:

(2RS,6E,8R,10R)-1-[4-(tert-butyldimethylsilyloxy)phenyl]-2-(N,N-dimethylamino)-8,10-dimethyldodec-6-en-3-one

(2RS,6E,8R,10R)-2-(N,N-dimethylamino)-1-(4-hydroxyphenyl)-8,10-dimethyldodec-6-en-3-one