11(S)-cyclohexyl-9,12-dioxo-2-oxa-10,13-diazabicyclo[14.3.1]eicosa-1⁽²⁰⁾,16,18-triene-14(S)-carboxylic acid

Base Information

• Chemical Name: 11(S)-cyclohexyl-9,12-dioxo-2-oxa-10,13-diazabicyclo[14.3.1]eicosa-1⁽²⁰⁾,16,18-triene-14(S)-carboxylic acid
• CAS No.: 371111-61-4
• Molecular Formula: C₂₄H₃₄N₂O₅
• Molecular Weight: 430.544

Synonyms:11(S)-cyclohexyl-9,12-dioxo-2-oxa-10,13-diazabicyclo[14.3.1]eicosa-1⁽²⁰⁾,16,18-triene-14(S)-carboxylic acid

Chemical Property of 11(S)-cyclohexyl-9,12-dioxo-2-oxa-10,13-diazabicyclo[14.3.1]eicosa-1⁽²⁰⁾,16,18-triene-14(S)-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 11(S)-cyclohexyl-9,12-dioxo-2-oxa-10,13-diazabicyclo[14.3.1]eicosa-1⁽²⁰⁾,16,18-triene-14(S)-carboxylic acid

There total 7 articles about 11(S)-cyclohexyl-9,12-dioxo-2-oxa-10,13-diazabicyclo[14.3.1]eicosa-1⁽²⁰⁾,16,18-triene-14(S)-carboxylic acid 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:

methyl 11(S)-cyclohexyl-9,12-dioxo-2-oxa-10,13-diazabicyclo[14.3.1]eicosa-1(20),16,18-triene-14(S)-carboxylate (371111-60-3) → 11(S)-cyclohexyl-9,12-dioxo-2-oxa-10,13-diazabicyclo[14.3.1]eicosa-1(20),16,18-triene-14(S)-carboxylic acid (371111-61-4)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; ethanol; at 20 ℃; for 3h;

DOI:10.1021/jm050323b

Reference yield:

[S,S]-2-(2-tert-butoxycarbonylamino-2-cyclohexylacetylamino)-3-(3-hydroxyphenyl)propionic acid methyl ester (371111-41-0) → 11(S)-cyclohexyl-9,12-dioxo-2-oxa-10,13-diazabicyclo[14.3.1]eicosa-1(20),16,18-triene-14(S)-carboxylic acid (371111-61-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: aq. HCl / dioxane / 4 h / 20 °C

2.1: 1.36 g / 3,4-dihydro-3-hydroxy-4-oxo-1,2,3-benzotriazine; 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; 4-methylmorpholine / dimethylformamide; CH₂Cl₂ / cooling

3.1: BH₃*THF / tetrahydrofuran / 1 h / 0 °C

3.2: 68 percent / aq. H₂O₂ / ethanol; tetrahydrofuran / 0 - 20 °C / pH 7

4.1: 68 percent / tri-n-butylphosphine; 1,1'-(azodicarbonyl)dipiperidine / CH₂Cl₂ / 4 h / 0 - 20 °C

5.1: aq. LiOH / tetrahydrofuran; ethanol / 3 h / 20 °C

With 4-methyl-morpholine; hydrogenchloride; lithium hydroxide; borane-THF; tributylphosphine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 3-hydroxy-3,4-dihydrobenzotriazine-4-one; 1,1'-azodicarbonyl-dipiperidine; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; N,N-dimethyl-formamide; 4.1: Mitsunobu reaction;

DOI:10.1021/jm050323b

Reference yield:

N-6-heptenoyl-(S)-cyclohexylglycine-(S)-m-tyrosine methyl ester (371111-58-9) → 11(S)-cyclohexyl-9,12-dioxo-2-oxa-10,13-diazabicyclo[14.3.1]eicosa-1(20),16,18-triene-14(S)-carboxylic acid (371111-61-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: BH₃*THF / tetrahydrofuran / 1 h / 0 °C

1.2: 68 percent / aq. H₂O₂ / ethanol; tetrahydrofuran / 0 - 20 °C / pH 7

2.1: 68 percent / tri-n-butylphosphine; 1,1'-(azodicarbonyl)dipiperidine / CH₂Cl₂ / 4 h / 0 - 20 °C

3.1: aq. LiOH / tetrahydrofuran; ethanol / 3 h / 20 °C

With lithium hydroxide; borane-THF; tributylphosphine; 1,1'-azodicarbonyl-dipiperidine; In tetrahydrofuran; ethanol; dichloromethane; 2.1: Mitsunobu reaction;

DOI:10.1021/jm050323b

upstream raw materials:

methyl 11(S)-cyclohexyl-9,12-dioxo-2-oxa-10,13-diazabicyclo[14.3.1]eicosa-1⁽²⁰⁾,16,18-triene-14(S)-carboxylate

[S,S]-2-(2-tert-butoxycarbonylamino-2-cyclohexylacetylamino)-3-(3-hydroxyphenyl)propionic acid methyl ester

N-6-heptenoyl-(S)-cyclohexylglycine-(S)-m-tyrosine methyl ester

N-7-hydroxyheptanoyl-(S)-cyclohexylglycine-(S)-m-tyrosine methyl ester

Downstream raw materials:

(S)-(2-{3-[((11S,14S)-11-Cyclohexyl-9,12-dioxo-2-oxa-10,13-diaza-bicyclo[14.3.1]icosa-1⁽¹⁹⁾,16⁽²⁰⁾,17-triene-14-carbonyl)-amino]-2-oxo-hexanoylamino}-acetylamino)-phenyl-acetic acid

(S)-(2-{3-[((11S,14S)-11-Cyclohexyl-9,12-dioxo-2-oxa-10,13-diaza-bicyclo[14.3.1]icosa-1⁽¹⁹⁾,16⁽²⁰⁾,17-triene-14-carbonyl)-amino]-2-oxo-hexanoylamino}-acetylamino)-phenyl-acetic acid tert-butyl ester

(S)-(2-{3-[((11S,14S)-11-Cyclohexyl-9,12-dioxo-2-oxa-10,13-diaza-bicyclo[14.3.1]icosa-1⁽¹⁹⁾,16⁽²⁰⁾,17-triene-14-carbonyl)-amino]-2-hydroxy-hexanoylamino}-acetylamino)-phenyl-acetic acid tert-butyl ester

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