allyl 5-hydroxy-2-{[(S)-2-(hydroxymethyl)pyrrolidinyl]carbonyl}-4-methoxyphenylcarbamate

Base Information

• Chemical Name: allyl 5-hydroxy-2-{[(S)-2-(hydroxymethyl)pyrrolidinyl]carbonyl}-4-methoxyphenylcarbamate
• CAS No.: 550355-92-5
• Molecular Formula: C₁₇H₂₂N₂O₆
• Molecular Weight: 350.371
• Mol file: 550355-92-5.mol

Synonyms:allyl 5-hydroxy-2-{[(S)-2-(hydroxymethyl)pyrrolidinyl]carbonyl}-4-methoxyphenylcarbamate

Chemical Property of allyl 5-hydroxy-2-{[(S)-2-(hydroxymethyl)pyrrolidinyl]carbonyl}-4-methoxyphenylcarbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of allyl 5-hydroxy-2-{[(S)-2-(hydroxymethyl)pyrrolidinyl]carbonyl}-4-methoxyphenylcarbamate

There total 4 articles about allyl 5-hydroxy-2-{[(S)-2-(hydroxymethyl)pyrrolidinyl]carbonyl}-4-methoxyphenylcarbamate 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: 85.0%

Allyl chloroformate (2937-50-0) + (S)-(2-amino-4-hydroxy-5-methoxyphenyl)(2-(hydroxymethyl)pyrrolidin-1-yl)methanone (550355-91-4) → allyl 5-hydroxy-2-{[(S)-2-(hydroxymethyl)pyrrolidinyl]carbonyl}-4-methoxyphenylcarbamate (550355-92-5)

Guidance literature:

With pyridine; In tetrahydrofuran; at -78 ℃; for 0.166667h;

DOI:10.1021/jm020526p

Reference yield:

4-(benzyloxy)-5-methoxy-2-nitrobenzoic acid (60547-92-4) → allyl 5-hydroxy-2-{[(S)-2-(hydroxymethyl)pyrrolidinyl]carbonyl}-4-methoxyphenylcarbamate (550355-92-5)

Guidance literature:

Multi-step reaction with 4 steps

1: (COCl)2 / dimethylformamide

2: K₂CO₃

3: H₂ / Pd/C / methanol / 0.92 h / 2585.74 Torr

4: 85 percent / pyridine / tetrahydrofuran / 0.17 h / -78 °C

With pyridine; oxalyl dichloride; hydrogen; potassium carbonate; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1021/jm020526p

Reference yield:

4-benzyloxy-5-methoxy-2-nitrobenzoyl chloride (64154-78-5) → allyl 5-hydroxy-2-{[(S)-2-(hydroxymethyl)pyrrolidinyl]carbonyl}-4-methoxyphenylcarbamate (550355-92-5)

Guidance literature:

Multi-step reaction with 3 steps

1: K₂CO₃

2: H₂ / Pd/C / methanol / 0.92 h / 2585.74 Torr

3: 85 percent / pyridine / tetrahydrofuran / 0.17 h / -78 °C

With pyridine; hydrogen; potassium carbonate; palladium on activated charcoal; In tetrahydrofuran; methanol;

DOI:10.1021/jm020526p

upstream raw materials:

Allyl chloroformate

(S)-(2-amino-4-hydroxy-5-methoxyphenyl)(2-(hydroxymethyl)pyrrolidin-1-yl)methanone

4-(benzyloxy)-5-methoxy-2-nitrobenzoic acid

4-benzyloxy-5-methoxy-2-nitrobenzoyl chloride

Downstream raw materials:

2,2,2-trichloroethyl 5-(5-{[(allyloxy)carbonyl]amino}-4-{[(2S)-2-(hydroxymethyl)pyrrolidinyl]carbonyl}-2-methoxyphenoxy)pentanoate

allyl 5-[3-(5-{[(allyloxy)carbonyl]amino}-4-{[(2S)-2-(hydroxymethyl)pyrrolidinyl]carbonyl}-2-methoxyphenoxy)propoxy]-2-{[(2S)-2-(hydroxymethyl)pyrrolidinyl]carbonyl}-4-methoxyphenylcarbamate

(2S)-1-(2-{[(allyloxy)carbonyl]amino}-5-methoxy-4-{[6-oxo-6-(2,2,2-trichloroethoxy)hexyl]oxy}benzoyl)-2-pyrrolidinecarboxylic acid

2,2,2-trichloroethyl 4-(5-{[(allyloxy)carbonyl]amino}-4-{[(2S)-2-(hydroxymethyl)pyrrolidinyl]carbonyl}-2-methoxyphenoxy)butanoate