(E)-(S)-4-tert-Butoxycarbonylamino-4-(4-methoxy-phenyl)-but-2-enoic acid ethyl ester

Base Information

• Chemical Name: (E)-(S)-4-tert-Butoxycarbonylamino-4-(4-methoxy-phenyl)-but-2-enoic acid ethyl ester
• CAS No.: 156324-99-1
• Molecular Formula: C₁₈H₂₅NO₅
• Molecular Weight: 335.4
• Mol file: 156324-99-1.mol

Synonyms:(E)-(S)-4-tert-Butoxycarbonylamino-4-(4-methoxy-phenyl)-but-2-enoic acid ethyl ester

Chemical Property of (E)-(S)-4-tert-Butoxycarbonylamino-4-(4-methoxy-phenyl)-but-2-enoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(S)-4-tert-Butoxycarbonylamino-4-(4-methoxy-phenyl)-but-2-enoic acid ethyl ester

There total 4 articles about (E)-(S)-4-tert-Butoxycarbonylamino-4-(4-methoxy-phenyl)-but-2-enoic acid ethyl ester 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:

N-(tert-butoxycarbonyl)-D-(4-hydroxyphenyl)glycine (27460-85-1) → (E)-(S)-4-tert-Butoxycarbonylamino-4-(4-methoxy-phenyl)-but-2-enoic acid ethyl ester (156324-99-1)

Guidance literature:

Multi-step reaction with 4 steps

1: (C₂H₅O)2P(O)CN, Et₃N / dimethylformamide / 18 h / 4 °C

2: K₂CO₃ / dimethylformamide / 7 h / Ambient temperature

3: 1M LAH / diethyl ether / 0.5 h / -15 - -7 °C

4: CH₂Cl₂ / 1 h / 0 °C

With lithium aluminium tetrahydride; diethyl cyanophosphonate; potassium carbonate; triethylamine; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)75803-5

Reference yield:

[(R)-(4-Hydroxy-phenyl)-(methoxy-methyl-carbamoyl)-methyl]-carbamic acid tert-butyl ester (156324-97-9) → (E)-(S)-4-tert-Butoxycarbonylamino-4-(4-methoxy-phenyl)-but-2-enoic acid ethyl ester (156324-99-1)

Guidance literature:

Multi-step reaction with 3 steps

1: K₂CO₃ / dimethylformamide / 7 h / Ambient temperature

2: 1M LAH / diethyl ether / 0.5 h / -15 - -7 °C

3: CH₂Cl₂ / 1 h / 0 °C

With lithium aluminium tetrahydride; potassium carbonate; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)75803-5

Reference yield:

[(R)-(Methoxy-methyl-carbamoyl)-(4-methoxy-phenyl)-methyl]-carbamic acid tert-butyl ester (156324-98-0) → (E)-(S)-4-tert-Butoxycarbonylamino-4-(4-methoxy-phenyl)-but-2-enoic acid ethyl ester (156324-99-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1M LAH / diethyl ether / 0.5 h / -15 - -7 °C

2: CH₂Cl₂ / 1 h / 0 °C

With lithium aluminium tetrahydride; In diethyl ether; dichloromethane;

DOI:10.1016/S0040-4039(00)75803-5

upstream raw materials:

(R)-(1-(4-methoxyphenyl)-2-oxoethyl) tert-butyl carbamate

ethyl (triphenylphosphoranylidene)acetate

N-(tert-butoxycarbonyl)-D-(4-hydroxyphenyl)glycine

[(R)-(4-Hydroxy-phenyl)-(methoxy-methyl-carbamoyl)-methyl]-carbamic acid tert-butyl ester

Downstream raw materials:

Acetic acid (1R,2R)-2,3-diacetoxy-1-[(R)-tert-butoxycarbonylamino-(4-methoxy-phenyl)-methyl]-propyl ester

Acetic acid (1S,2S)-2,3-diacetoxy-1-[(R)-tert-butoxycarbonylamino-(4-methoxy-phenyl)-methyl]-propyl ester

[(E)-(S)-4-Hydroxy-1-(4-methoxy-phenyl)-but-2-enyl]-carbamic acid tert-butyl ester