(S,S)-3-cyclohexyl-2,5-dioxo-12-oxa-1,4-diazatricyclo[11.5.3.0^16,20]henicosa-13⁽²¹⁾,14,16⁽²⁰⁾-triene-18-carboxylic acid methyl ester

Base Information

• Chemical Name: (S,S)-3-cyclohexyl-2,5-dioxo-12-oxa-1,4-diazatricyclo[11.5.3.0^16,20]henicosa-13⁽²¹⁾,14,16⁽²⁰⁾-triene-18-carboxylic acid methyl ester
• CAS No.: 367259-38-9
• Molecular Formula: C₂₆H₃₆N₂O₅
• Molecular Weight: 456.582

Synonyms:(S,S)-3-cyclohexyl-2,5-dioxo-12-oxa-1,4-diazatricyclo[11.5.3.0^16,20]henicosa-13⁽²¹⁾,14,16⁽²⁰⁾-triene-18-carboxylic acid methyl ester

Chemical Property of (S,S)-3-cyclohexyl-2,5-dioxo-12-oxa-1,4-diazatricyclo[11.5.3.0^16,20]henicosa-13⁽²¹⁾,14,16⁽²⁰⁾-triene-18-carboxylic acid methyl ester

Chemical Property:

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Technology Process of (S,S)-3-cyclohexyl-2,5-dioxo-12-oxa-1,4-diazatricyclo[11.5.3.0^16,20]henicosa-13⁽²¹⁾,14,16⁽²⁰⁾-triene-18-carboxylic acid methyl ester

There total 6 articles about (S,S)-3-cyclohexyl-2,5-dioxo-12-oxa-1,4-diazatricyclo[11.5.3.0^16,20]henicosa-13⁽²¹⁾,14,16⁽²⁰⁾-triene-18-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: 66.0%

(S,S)-2-[2-cyclohexyl-2-(7-hydroxyheptanoylamino)acetyl]-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid methyl ester (367259-37-8) → (S,S)-3-cyclohexyl-2,5-dioxo-12-oxa-1,4-diazatricyclo[11.5.3.016,20]henicosa-13(21),14,16(20)-triene-18-carboxylic acid methyl ester (367259-38-9)

Guidance literature:

With triphenylphosphine; 1,1'-azodicarbonyl-dipiperidine; In dichloromethane; at 0 - 20 ℃; for 82.33h;

DOI:10.1021/jm050520a

Reference yield:

(S,S)-2-(2-cyclohexyl-2-hept-6-enoylaminoacetyl)-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid methyl ester (367259-36-7) → (S,S)-3-cyclohexyl-2,5-dioxo-12-oxa-1,4-diazatricyclo[11.5.3.016,20]henicosa-13(21),14,16(20)-triene-18-carboxylic acid methyl ester (367259-38-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: borane*THF / tetrahydrofuran / 1.67 h / 0 °C

1.2: 93 percent / aq. H₂O₂; ethanol / tetrahydrofuran / 2.33 h / 0 - 20 °C / pH 7

2.1: 66 percent / 1,1'-(azodicarbonyl)dipiperidine; triphenylphosphine / CH₂Cl₂ / 82.33 h / 0 - 20 °C

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

DOI:10.1021/jm050520a

Reference yield:

N-(tert-butoxycarbonyl)-L-cyclohexylglycine (109183-71-3) → (S,S)-3-cyclohexyl-2,5-dioxo-12-oxa-1,4-diazatricyclo[11.5.3.016,20]henicosa-13(21),14,16(20)-triene-18-carboxylic acid methyl ester (367259-38-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 97 percent / 3-hydroxy-1,2,3-benzotriazin-4(3H)-one; 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; 4-methylmorpholine / dimethylformamide; CH₂Cl₂ / -20 °C

2.1: HCl / dioxane / 4 h / 20 °C

3.1: 2.30 g / 3-hydroxy-1,2,3-benzotriazin-4(3H)-one; 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; 4-methylmorpholine / dimethylformamide; CH₂Cl₂ / -20 °C

4.1: borane*THF / tetrahydrofuran / 1.67 h / 0 °C

4.2: 93 percent / aq. H₂O₂; ethanol / tetrahydrofuran / 2.33 h / 0 - 20 °C / pH 7

5.1: 66 percent / 1,1'-(azodicarbonyl)dipiperidine; triphenylphosphine / CH₂Cl₂ / 82.33 h / 0 - 20 °C

With 4-methyl-morpholine; hydrogenchloride; borane-THF; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 3-hydroxy-3,4-dihydrobenzotriazine-4-one; triphenylphosphine; 1,1'-azodicarbonyl-dipiperidine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; 5.1: Mitsunobu reaction;

DOI:10.1021/jm050520a

upstream raw materials:

(S,S)-2-[2-cyclohexyl-2-(7-hydroxyheptanoylamino)acetyl]-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid methyl ester

(S,S)-2-(2-cyclohexyl-2-hept-6-enoylaminoacetyl)-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid methyl ester

N-(tert-butoxycarbonyl)-L-cyclohexylglycine

(S,S)-2-(2-tert-butoxycarbonylamino-2-cyclohexylacetyl)-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid methyl ester

Downstream raw materials:

(S,S)-3-cyclohexyl-2,5-dioxo-12-oxa-1,4-diazatricyclo[11.5.3.0^16,20]henicosa-13⁽²¹⁾,14,16⁽²⁰⁾-triene-18-carboxylic acid

(3S,18S)-3-Cyclohexyl-2,5-dioxo-12-oxa-1,4-diaza-tricyclo[11.5.3.0^16,20]henicosa-13⁽²¹⁾,14,16⁽²⁰⁾-triene-18-carboxylic acid [1-(carbamoyl-hydroxy-methyl)-butyl]-amide

{3-[((3S,18S)-3-Cyclohexyl-2,5-dioxo-12-oxa-1,4-diaza-tricyclo[11.5.3.0^16,20]henicosa-13⁽²¹⁾,14,16⁽²⁰⁾-triene-18-carbonyl)-amino]-2-oxo-hexanoylamino}-acetic acid

{3-[((3S,18S)-3-Cyclohexyl-2,5-dioxo-12-oxa-1,4-diaza-tricyclo[11.5.3.0^16,20]henicosa-13⁽²¹⁾,14,16⁽²⁰⁾-triene-18-carbonyl)-amino]-2-hydroxy-hexanoylamino}-acetic acid benzyl ester

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