12-cyclohexyl-11,14-dioxo-2-oxa-6-thia-10,13-diazatricyclo[14.3.1.1^7,10]henicosa-1⁽¹⁹⁾,16⁽²⁰⁾,17-triene-9-carboxylic acid methyl ester

Base Information

• Chemical Name: 12-cyclohexyl-11,14-dioxo-2-oxa-6-thia-10,13-diazatricyclo[14.3.1.1^7,10]henicosa-1⁽¹⁹⁾,16⁽²⁰⁾,17-triene-9-carboxylic acid methyl ester
• CAS No.: 367258-60-4
• Molecular Formula: C₂₅H₃₄N₂O₅S
• Molecular Weight: 474.621

Synonyms:12-cyclohexyl-11,14-dioxo-2-oxa-6-thia-10,13-diazatricyclo[14.3.1.1^7,10]henicosa-1⁽¹⁹⁾,16⁽²⁰⁾,17-triene-9-carboxylic acid methyl ester

Chemical Property of 12-cyclohexyl-11,14-dioxo-2-oxa-6-thia-10,13-diazatricyclo[14.3.1.1^7,10]henicosa-1⁽¹⁹⁾,16⁽²⁰⁾,17-triene-9-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

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Technology Process of 12-cyclohexyl-11,14-dioxo-2-oxa-6-thia-10,13-diazatricyclo[14.3.1.1^7,10]henicosa-1⁽¹⁹⁾,16⁽²⁰⁾,17-triene-9-carboxylic acid methyl ester

There total 7 articles about 12-cyclohexyl-11,14-dioxo-2-oxa-6-thia-10,13-diazatricyclo[14.3.1.1^7,10]henicosa-1⁽¹⁹⁾,16⁽²⁰⁾,17-triene-9-carboxylic acid methyl 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: 22.0%

(2S,4R)-1-{(S)-2-Cyclohexyl-2-[2-(3-hydroxy-phenyl)-acetylamino]-acetyl}-4-(3-hydroxy-propylsulfanyl)-pyrrolidine-2-carboxylic acid methyl ester (367260-69-3) → 12-cyclohexyl-11,14-dioxo-2-oxa-6-thia-10,13-diazatricyclo[14.3.1.17,10]henicosa-1(19),16(20),17-triene-9-carboxylic acid methyl ester (367258-60-4)

Guidance literature:

With triphenylphosphine; 1,1'-azodicarbonyl-dipiperidine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/jo011160b

Reference yield:

(2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester (74844-91-0,114676-69-6,135042-17-0,227935-38-8,102195-79-9) → 12-cyclohexyl-11,14-dioxo-2-oxa-6-thia-10,13-diazatricyclo[14.3.1.17,10]henicosa-1(19),16(20),17-triene-9-carboxylic acid methyl ester (367258-60-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 97 percent / Et₃N; DMAP / CH₂Cl₂ / 0 - 20 °C

2: 78 percent / NaH / dimethylformamide / 0 - 20 °C

3: 4 M HCl / dioxane / 1 h / 0 °C

4: HOOBt; EDCI; NMM / dimethylformamide; CH₂Cl₂ / 48 h / -8 °C

5: 4 M HCl / dioxane / 20 °C

6: HOOBt; EDCI; NMM / dimethylformamide; CH₂Cl₂ / -20 - -10 °C

7: 22 percent / ADDP; PPh₃ / CH₂Cl₂ / 0 - 20 °C

With 4-methyl-morpholine; hydrogenchloride; dmap; sodium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 3-hydroxy-3,4-dihydrobenzotriazine-4-one; triphenylphosphine; 1,1'-azodicarbonyl-dipiperidine; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; 7: intramolecular Mitsunobu reaction;

DOI:10.1021/jo011160b

Reference yield:

(2S,4R)-4-[(3-hydroxypropyl)thio]-1,2-pyrrolidinedicarboxylic acid 1-(1,1-dimethylethyl) 2-methyl ester (367259-60-7) → 12-cyclohexyl-11,14-dioxo-2-oxa-6-thia-10,13-diazatricyclo[14.3.1.17,10]henicosa-1(19),16(20),17-triene-9-carboxylic acid methyl ester (367258-60-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 4 M HCl / dioxane / 1 h / 0 °C

2: HOOBt; EDCI; NMM / dimethylformamide; CH₂Cl₂ / 48 h / -8 °C

3: 4 M HCl / dioxane / 20 °C

4: HOOBt; EDCI; NMM / dimethylformamide; CH₂Cl₂ / -20 - -10 °C

5: 22 percent / ADDP; PPh₃ / CH₂Cl₂ / 0 - 20 °C

With 4-methyl-morpholine; hydrogenchloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 3-hydroxy-3,4-dihydrobenzotriazine-4-one; triphenylphosphine; 1,1'-azodicarbonyl-dipiperidine; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; 5: intramolecular Mitsunobu reaction;

DOI:10.1021/jo011160b

upstream raw materials:

(2S,4R)-1-{(S)-2-Cyclohexyl-2-[2-(3-hydroxy-phenyl)-acetylamino]-acetyl}-4-(3-hydroxy-propylsulfanyl)-pyrrolidine-2-carboxylic acid methyl ester

(2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester

(2S,4R)-4-[(3-hydroxypropyl)thio]-1,2-pyrrolidinedicarboxylic acid 1-(1,1-dimethylethyl) 2-methyl ester

1-tert-butyl 2-methyl (2S,4S)-4-{[(4-bromo-phenyl)sulfonyl]oxy}-pyrrolidine-1,2-dicarboxylate

Downstream raw materials:

12-cyclohexyl-11,14-dioxo-2-oxa-6-thia-10,13-diazatricyclo[14.3.1.1^7,10]henicosa-1⁽¹⁹⁾,16⁽²⁰⁾,17-triene-9-carboxylic acid

12-cyclohexyl-6,6,11,14-tetraoxo-2-oxa-6λ⁶-thia-10,13-diazatricyclo[14.3.1.1^7,10]henicosa-1(19),16(20),17-triene-9-carboxylic acid methyl ester

12-cyclohexyl-6,6,11,14-tetraoxo-2-oxa-6λ⁶-thia-10,13-diazatricyclo[14.3.1.1^7,10]henicosa-1(19),16(20),17-triene-9-carboxylic acid

(7R,9S,12S)-12-Cyclohexyl-11,14-dioxo-2-oxa-6-thia-10,13-diaza-tricyclo[14.3.1.1^7,10]henicosa-1⁽²⁰⁾,16,18-triene-9-carboxylic acid {1-[({[((S)-dimethylcarbamoyl-phenyl-methyl)-carbamoyl]-methyl}-carbamoyl)-hydroxy-methyl]-butyl}-amide

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