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

Base Information

• Chemical Name: methyl 11(S)-cyclohexyl-9,12-dioxo-2-oxa-10,13-diazabicyclo[14.3.1]eicosa-1⁽²⁰⁾,16,18-triene-14(S)-carboxylate
• CAS No.: 371111-60-3
• Molecular Formula: C₂₅H₃₆N₂O₅
• Molecular Weight: 444.571

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

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

Chemical Property:

Purity/Quality:

Safty Information:

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

There total 6 articles about methyl 11(S)-cyclohexyl-9,12-dioxo-2-oxa-10,13-diazabicyclo[14.3.1]eicosa-1⁽²⁰⁾,16,18-triene-14(S)-carboxylate 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: 68.0%

N-7-hydroxyheptanoyl-(S)-cyclohexylglycine-(S)-m-tyrosine methyl ester (371111-59-0) → 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)

Guidance literature:

With tributylphosphine; 1,1'-azodicarbonyl-dipiperidine; In dichloromethane; at 0 - 20 ℃; for 4h;

DOI:10.1021/jm050323b

Reference yield:

[S,S]-2-(2-tert-butoxycarbonylamino-2-cyclohexylacetylamino)-3-(3-hydroxyphenyl)propionic acid methyl ester (371111-41-0) → 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)

Guidance literature:

Multi-step reaction with 4 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

With 4-methyl-morpholine; hydrogenchloride; 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; 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) → 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)

Guidance literature:

Multi-step reaction with 2 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

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

DOI:10.1021/jm050323b

upstream raw materials:

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

[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-(tert-butoxycarbonyl)-L-cyclohexylglycine

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 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

(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

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

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