(S)-benzyl 2<(tert-butyloxycarbonyl)amino>-7-phenylheptanoate

Base Information

• Chemical Name: (S)-benzyl 2<(tert-butyloxycarbonyl)amino>-7-phenylheptanoate
• CAS No.: 150722-83-1
• Molecular Formula: C₂₅H₃₃NO₄
• Molecular Weight: 411.541
• Mol file: 150722-83-1.mol

Synonyms:(S)-benzyl 2<(tert-butyloxycarbonyl)amino>-7-phenylheptanoate

Chemical Property of (S)-benzyl 2<(tert-butyloxycarbonyl)amino>-7-phenylheptanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-benzyl 2<(tert-butyloxycarbonyl)amino>-7-phenylheptanoate

There total 12 articles about (S)-benzyl 2<(tert-butyloxycarbonyl)amino>-7-phenylheptanoate 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:

di-tert-butyl dicarbonate (24424-99-5) → (S)-benzyl 2<(tert-butyloxycarbonyl)amino>-7-phenylheptanoate (150722-83-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 1 N aq. NaOH / dioxane

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

3: diethyl ether / 0.5 h / 0 °C

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

5: 1 N NaOH / methanol / 0.5 h / 40 °C

6: 1,8-diazabicyclo<5.4.0>undec-7-ene / benzene / 2 h / Heating

With 4-methyl-morpholine; sodium hydroxide; silver benzoate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; isobutyl chloroformate; In 1,4-dioxane; methanol; 1,2-dimethoxyethane; diethyl ether; benzene;

DOI:10.1021/jm00072a024

Reference yield:

1-Bromo-4-phenylbutane (13633-25-5) → (S)-benzyl 2<(tert-butyloxycarbonyl)amino>-7-phenylheptanoate (150722-83-1)

Guidance literature:

Multi-step reaction with 11 steps

1: 1.) Na / 1.) EtOH, 0 deg C, 5 min, 2.) EtOH, reflux, 6 h

2: 92 percent / 1 M NaOH / ethanol / 0.5 h / Ambient temperature

3: 98 percent / 0.17 h / 130 °C

4: 90 percent / aq. KCl / dimethylsulfoxide / 8 h / 39 °C / Subtilisin Carlsberg enzyme

5: 96 percent / 6 N aq. HCl / 4 h / Heating

6: 1 N aq. NaOH / dioxane

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

8: diethyl ether / 0.5 h / 0 °C

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

10: 1 N NaOH / methanol / 0.5 h / 40 °C

11: 1,8-diazabicyclo<5.4.0>undec-7-ene / benzene / 2 h / Heating

With 4-methyl-morpholine; hydrogenchloride; sodium hydroxide; potassium chloride; silver benzoate; sodium; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; isobutyl chloroformate; In 1,4-dioxane; methanol; 1,2-dimethoxyethane; diethyl ether; ethanol; dimethyl sulfoxide; benzene;

DOI:10.1021/jm00072a024

Reference yield:

(S)-2-acetamido-6-phenylhexanoic acid (150823-78-2) → (S)-benzyl 2<(tert-butyloxycarbonyl)amino>-7-phenylheptanoate (150722-83-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 96 percent / 6 N aq. HCl / 4 h / Heating

2: 1 N aq. NaOH / dioxane

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

4: diethyl ether / 0.5 h / 0 °C

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

6: 1 N NaOH / methanol / 0.5 h / 40 °C

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

With 4-methyl-morpholine; hydrogenchloride; sodium hydroxide; silver benzoate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; isobutyl chloroformate; In 1,4-dioxane; methanol; 1,2-dimethoxyethane; diethyl ether; benzene;

DOI:10.1021/jm00072a024

upstream raw materials:

benzyl bromide

(S)-2<(tert-butyloxycarbonyl)amino>-7-phenylheptanoic acid

di-tert-butyl dicarbonate

1-Bromo-4-phenylbutane

Downstream raw materials:

Boc-Nle-(S)-β-homo-Aph-OBzl

Refernces