acetylamino-(3-phenoxy-propyl)-malonic acid diethyl ester

Base Information

• Chemical Name: acetylamino-(3-phenoxy-propyl)-malonic acid diethyl ester
• CAS No.: 150722-71-7
• Molecular Formula: C₁₈H₂₅NO₆
• Molecular Weight: 351.4
• Mol file: 150722-71-7.mol

Synonyms:acetylamino-(3-phenoxy-propyl)-malonic acid diethyl ester

Chemical Property of acetylamino-(3-phenoxy-propyl)-malonic acid diethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of acetylamino-(3-phenoxy-propyl)-malonic acid diethyl ester

There total 1 articles about acetylamino-(3-phenoxy-propyl)-malonic acid diethyl 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:

3-phenoxypropyl bromide (588-63-6) + 2-acetylaminomalonic acid diethyl ester (1068-90-2) → acetylamino-(3-phenoxy-propyl)-malonic acid diethyl ester (150722-71-7)

Guidance literature:

With ethanol; sodium ethanolate;

Reference yield:

acetylamino-(3-phenoxy-propyl)-malonic acid diethyl ester (150722-71-7) → Boc-Tyr-Nle-Gly-Trp-Nle-(S)-β-homo-App-OH

Guidance literature:

Multi-step reaction with 16 steps

1: 1 M NaOH / ethanol / 0.5 h / Ambient temperature

2: 0.17 h / 130 °C

3: aq. KCl / dimethylsulfoxide / 8 h / 39 °C / Subtilisin Carlsberg enzyme

4: 6 N aq. HCl / 4 h / Heating

5: 1 N aq. NaOH / dioxane

6: isobutylchloroformiate, N-methylmorpholine / 1,2-dimethoxy-ethane / 0.08 h / -15 °C

7: diethyl ether / 0.5 h / 0 °C

8: silver benzoate, triethylamine / 0.5 h / Ambient temperature

9: 1 N NaOH / methanol / 0.5 h / 40 °C

10: 1,8-diazabicyclo<5.4.0>undec-7-ene / benzene / 2 h / Heating

11: trifluoroacetic acid / 0.5 h / Ambient temperature

12: (benzotriazolyloxy)tris(dimethylamino)phosphonium hexafluorophosphate, N-methylmorpholine / dimethylformamide / 1 h / Ambient temperature

13: trifluoroacetic acid / 0.5 h / Ambient temperature

14: (benzotriazolyloxy)tris(dimethylamino)phosphonium hexafluorophosphate, N-methylmorpholine / dimethylformamide / 1 h / Ambient temperature

15: H₂ / 10percent Pd/C / dimethylformamide; acetic acid; H₂O / 760 Torr / Ambient temperature

16: dimethylformamide / 3 h / Ambient temperature

With 4-methyl-morpholine; hydrogenchloride; sodium hydroxide; potassium chloride; hydrogen; silver benzoate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; trifluoroacetic acid; isobutyl chloroformate; palladium on activated charcoal; In 1,4-dioxane; methanol; 1,2-dimethoxyethane; diethyl ether; ethanol; water; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jm00072a024

Reference yield:

acetylamino-(3-phenoxy-propyl)-malonic acid diethyl ester (150722-71-7) → Boc-Tyr(SO3H)-Nle-Gly-(D)-Trp-Nle-(R)-β-homo-App-OH

Guidance literature:

Multi-step reaction with 17 steps

1: 1 M NaOH / ethanol / 0.5 h / Ambient temperature

2: 0.17 h / 130 °C

4: 6 N aq. HCl / 4 h / Heating

5: 1N aq. NaOH / dioxane

6: isobutylchloroformiate, N-methylmorpholine / 1,2-dimethoxy-ethane / 0.08 h / -15 °C

7: diethyl ether / 0.5 h / 0 °C

8: silver benzoate, triethylamine / 0.5 h / Ambient temperature

9: 1 N NaOH / methanol / 0.5 h / 40 °C

10: 1,8-diazabicyclo<5.4.0>undec-7-ene / benzene / 2 h / Heating

11: trifluoroacetic acid / 0.5 h / Ambient temperature

12: (benzotriazolyloxy)tris(dimethylamino)phosphonium hexafluorophosphate, N-methylmorpholine / dimethylformamide / 1 h / Ambient temperature

13: trifluoroacetic acid / 0.5 h / Ambient temperature

14: (benzotriazolyloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP), N-methylmorpholine (NMM) / dimethylformamide / 1 h / Ambient temperature

15: H₂ / 10percent Pd/C / dimethylformamide; acetic acid; H₂O / 760 Torr / Ambient temperature

16: dimethylformamide / 3 h / Ambient temperature

17: SO₃-pyridine complex / dimethylformamide / Ambient temperature

With 4-methyl-morpholine; hydrogenchloride; sodium hydroxide; pyridine-SO₃ complex; hydrogen; silver benzoate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; trifluoroacetic acid; isobutyl chloroformate; palladium on activated charcoal; In 1,4-dioxane; methanol; 1,2-dimethoxyethane; diethyl ether; ethanol; water; acetic acid; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jm00072a024

upstream raw materials:

3-phenoxypropyl bromide

2-acetylaminomalonic acid diethyl ester

Downstream raw materials:

5-phenoxy-norvaline

N-acetyl-5-phenoxy-norvaline

(S)-2-Acetylamino-5-phenoxy-pentanoic acid

Refernces