{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

Base Information

• Chemical Name: {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
• CAS No.: 875877-47-7
• Molecular Formula: C₄₀H₅₄N₄O₈
• Molecular Weight: 718.891

Synonyms:{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

Chemical Property of {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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Technology Process of {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

There total 12 articles about {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 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%

(3-amino-2-hydroxyhexanoylamino)acetic acid benzyl ester hydrochloride + (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 (367259-39-0) → {3-[((3S,18S)-3-Cyclohexyl-2,5-dioxo-12-oxa-1,4-diaza-tricyclo[11.5.3.016,20]henicosa-13(21),14,16(20)-triene-18-carbonyl)-amino]-2-hydroxy-hexanoylamino}-acetic acid benzyl ester (875877-47-7)

Guidance literature:

With 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 3-hydroxy-3,4-dihydrobenzotriazine-4-one; In dichloromethane; N,N-dimethyl-formamide; at -20 ℃;

DOI:10.1021/jm050520a

Reference yield:

2-hydroxy-3-nitrohexanoic acid (367258-42-2) → {3-[((3S,18S)-3-Cyclohexyl-2,5-dioxo-12-oxa-1,4-diaza-tricyclo[11.5.3.016,20]henicosa-13(21),14,16(20)-triene-18-carbonyl)-amino]-2-hydroxy-hexanoylamino}-acetic acid benzyl ester (875877-47-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 66 percent / H₂; acetic acid / Pd/C / 20 h / 20 °C / 3051.17 Torr

2.1: aq. NaOH / dioxane / 0.17 h / 0 °C

2.2: 89 percent / dioxane; H₂O / 1 h / 0 - 20 °C

3.1: 95 percent / 3-hydroxy-1,2,3-benzotriazin-4(3H)-one; 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; 4-methylmorpholine / dimethylformamide; CH₂Cl₂ / -20 °C

4.1: 100 percent / HCl / dioxane / 3 h / 20 °C

5.1: 66 percent / 3-hydroxy-1,2,3-benzotriazin-4(3H)-one; 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; 4-methylmorpholine / dimethylformamide; CH₂Cl₂ / -20 °C

With 4-methyl-morpholine; hydrogenchloride; sodium hydroxide; hydrogen; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 3-hydroxy-3,4-dihydrobenzotriazine-4-one; palladium on activated charcoal; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm050520a

Reference yield:

3-tert-butoxycarbonylamino-2-hydroxyhexanoic acid (166196-06-1) → {3-[((3S,18S)-3-Cyclohexyl-2,5-dioxo-12-oxa-1,4-diaza-tricyclo[11.5.3.016,20]henicosa-13(21),14,16(20)-triene-18-carbonyl)-amino]-2-hydroxy-hexanoylamino}-acetic acid benzyl ester (875877-47-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / 3-hydroxy-1,2,3-benzotriazin-4(3H)-one; 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; 4-methylmorpholine / dimethylformamide; CH₂Cl₂ / -20 °C

2: 100 percent / HCl / dioxane / 3 h / 20 °C

3: 66 percent / 3-hydroxy-1,2,3-benzotriazin-4(3H)-one; 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; 4-methylmorpholine / dimethylformamide; CH₂Cl₂ / -20 °C

With 4-methyl-morpholine; hydrogenchloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 3-hydroxy-3,4-dihydrobenzotriazine-4-one; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm050520a

upstream 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

2-hydroxy-3-nitrohexanoic acid

3-tert-butoxycarbonylamino-2-hydroxyhexanoic acid

(3-tert-butoxycarbonylamino-2-hydroxyhexanoylamino)acetic acid benzyl ester

Downstream raw materials:

{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-oxo-hexanoylamino}-acetic acid benzyl ester

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