12-cyclohexyl-11,14-dioxo-2,6-dioxa-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-2,6-dioxa-10,13-diazatricyclo[14.3.1.1^7,10]henicosa-1⁽¹⁹⁾,16⁽²⁰⁾,17-triene-9-carboxylic acid methyl ester
• CAS No.: 367258-55-7
• Molecular Formula: C₂₅H₃₄N₂O₆
• Molecular Weight: 458.555

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

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

There total 9 articles about 12-cyclohexyl-11,14-dioxo-2,6-dioxa-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: 35.0%

methyl (2S,4R)-1-[(2S)-2-cyclohexyl-2-[[(3-hydroxyphenyl)acetyl]amino]-1-oxoethyl]-4-(3-hydroxypropoxy)-2-pyrrolidinecarboxylate (367258-54-6) → 12-cyclohexyl-11,14-dioxo-2,6-dioxa-10,13-diazatricyclo[14.3.1.17,10]henicosa-1(19),16(20),17-triene-9-carboxylic acid methyl ester (367258-55-7)

Guidance literature:

With triphenylphosphine; 1,1'-azodicarbonyl-dipiperidine; In dichloromethane; at 0 - 20 ℃; for 24h;

DOI:10.1021/jo011160b

Reference yield:

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid (13726-69-7,946610-68-0) → 12-cyclohexyl-11,14-dioxo-2,6-dioxa-10,13-diazatricyclo[14.3.1.17,10]henicosa-1(19),16(20),17-triene-9-carboxylic acid methyl ester (367258-55-7)

Guidance literature:

Multi-step reaction with 8 steps

1: NaH; NaI / dimethylformamide / 18 h / 20 °C

2: 5.15 g / benzene; methanol; hexane / 1 h / 20 °C

3: 4 M HCl / dioxane / 5 h / 20 °C

4: 6.60 g / HOOBt; EDCI; NMM / dimethylformamide; CH₂Cl₂ / 18.5 h / -20 - -10 °C

5: 4 M HCl / dioxane / 4 h / 20 °C

6: 6.30 g / HOOBt; EDCI; NMM / dimethylformamide; CH₂Cl₂ / 18.5 h / -20 - -10 °C

7: 87 percent / H₂ / 10percent Pd/C / ethanol / 23 h / 20 °C

8: 35 percent / ADDP; PPh₃ / CH₂Cl₂ / 24 h / 0 - 20 °C

With 4-methyl-morpholine; hydrogenchloride; hydrogen; sodium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 3-hydroxy-3,4-dihydrobenzotriazine-4-one; triphenylphosphine; sodium iodide; 1,1'-azodicarbonyl-dipiperidine; 10percent Pd/C; In 1,4-dioxane; methanol; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; benzene; 8: intramolecular Mitsunobu reaction;

DOI:10.1021/jo011160b

Reference yield:

(2S,4R)-4-[3-(phenylmethoxy)propoxy]-1,2-pyrrolidinedicarboxylic acid 1-(1,1-dimethylethyl) 2-methyl ester (367259-54-9) → 12-cyclohexyl-11,14-dioxo-2,6-dioxa-10,13-diazatricyclo[14.3.1.17,10]henicosa-1(19),16(20),17-triene-9-carboxylic acid methyl ester (367258-55-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 4 M HCl / dioxane / 5 h / 20 °C

2: 6.60 g / HOOBt; EDCI; NMM / dimethylformamide; CH₂Cl₂ / 18.5 h / -20 - -10 °C

3: 4 M HCl / dioxane / 4 h / 20 °C

4: 6.30 g / HOOBt; EDCI; NMM / dimethylformamide; CH₂Cl₂ / 18.5 h / -20 - -10 °C

5: 87 percent / H₂ / 10percent Pd/C / ethanol / 23 h / 20 °C

6: 35 percent / ADDP; PPh₃ / CH₂Cl₂ / 24 h / 0 - 20 °C

With 4-methyl-morpholine; hydrogenchloride; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 3-hydroxy-3,4-dihydrobenzotriazine-4-one; triphenylphosphine; 1,1'-azodicarbonyl-dipiperidine; 10percent Pd/C; In 1,4-dioxane; ethanol; dichloromethane; N,N-dimethyl-formamide; 6: intramolecular Mitsunobu reaction;

DOI:10.1021/jo011160b

upstream raw materials:

methyl (2S,4R)-1-[(2S)-2-cyclohexyl-2-[[(3-hydroxyphenyl)acetyl]amino]-1-oxoethyl]-4-(3-hydroxypropoxy)-2-pyrrolidinecarboxylate

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

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

(2S,4R)-4-(3-Benzyloxy-propoxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

Downstream raw materials:

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

3-[((7R,9S,12S)-12-Cyclohexyl-11,14-dioxo-2,6-dioxa-10,13-diaza-tricyclo[14.3.1.1^7,10]henicosa-1⁽²⁰⁾,16,18-triene-9-carbonyl)-amino]-2-oxo-hexanoic acid tert-butyl ester

{3-[((7R,9S,12S)-12-Cyclohexyl-11,14-dioxo-2,6-dioxa-10,13-diaza-tricyclo[14.3.1.1^7,10]henicosa-1⁽²⁰⁾,16,18-triene-9-carbonyl)-amino]-2-oxo-hexanoylamino}-acetic acid

{3-[((7R,9S,12S)-12-Cyclohexyl-11,14-dioxo-2,6-dioxa-10,13-diaza-tricyclo[14.3.1.1^7,10]henicosa-1⁽²⁰⁾,16,18-triene-9-carbonyl)-amino]-2-hydroxy-hexanoylamino}-acetic acid benzyl ester

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