L-valyl-N-{[1-(2-{[(4S)-10-bromo-4-ethyl-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3',4’:6,7]indolizino[1,2-b]quinolin-4-yl]oxy}-2-oxoethyl)cyclohexyl]methyl}-N⁵-carbamoyl-L-ornithinamide

Base Information

• Chemical Name: L-valyl-N-{[1-(2-{[(4S)-10-bromo-4-ethyl-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3',4’:6,7]indolizino[1,2-b]quinolin-4-yl]oxy}-2-oxoethyl)cyclohexyl]methyl}-N⁵-carbamoyl-L-ornithinamide
• CAS No.: 1609075-27-5
• Molecular Formula: C₄₀H₅₀BrN₇O₈
• Molecular Weight: 836.783

Synonyms:L-valyl-N-{[1-(2-{[(4S)-10-bromo-4-ethyl-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3',4’:6,7]indolizino[1,2-b]quinolin-4-yl]oxy}-2-oxoethyl)cyclohexyl]methyl}-N⁵-carbamoyl-L-ornithinamide

Chemical Property of L-valyl-N-{[1-(2-{[(4S)-10-bromo-4-ethyl-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3',4’:6,7]indolizino[1,2-b]quinolin-4-yl]oxy}-2-oxoethyl)cyclohexyl]methyl}-N⁵-carbamoyl-L-ornithinamide

Chemical Property:

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Technology Process of L-valyl-N-{[1-(2-{[(4S)-10-bromo-4-ethyl-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3',4’:6,7]indolizino[1,2-b]quinolin-4-yl]oxy}-2-oxoethyl)cyclohexyl]methyl}-N⁵-carbamoyl-L-ornithinamide

There total 1 articles about L-valyl-N-{[1-(2-{[(4S)-10-bromo-4-ethyl-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3',4’:6,7]indolizino[1,2-b]quinolin-4-yl]oxy}-2-oxoethyl)cyclohexyl]methyl}-N⁵-carbamoyl-L-ornithinamide 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:

→ L-valyl-N-{[1-(2-{[(4S)-10-bromo-4-ethyl-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3',4’:6,7]indolizino[1,2-b]quinolin-4-yl]oxy}-2-oxoethyl)cyclohexyl]methyl}-N5-carbamoyl-L-ornithinamide (1609075-27-5)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; at 20 ℃; for 0.5h;

Reference yield: 78.0%

2,5-Dihydro-2,5-dioxo-1H-pyrrole-1-hexanoic acid (55750-53-3) + L-valyl-N-{[1-(2-{[(4S)-10-bromo-4-ethyl-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3',4’:6,7]indolizino[1,2-b]quinolin-4-yl]oxy}-2-oxoethyl)cyclohexyl]methyl}-N5-carbamoyl-L-ornithinamide (1609075-27-5) → N-[6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoyl]-L-valyl-N-{[1-(2-{[(4S)-10-bromo-4-ethyl-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3',4':6,7]indol izino[1,2-b]quinolin-4-yl]oxy}-2-oxoethyl)cyclohexyl]methyl}-N5-carbamoyl-L-ornithinamide (1609075-30-0)

Guidance literature:

2,5-Dihydro-2,5-dioxo-1H-pyrrole-1-hexanoic acid; With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; at 20 ℃; for 3h;

L-valyl-N-{[1-(2-{[(4S)-10-bromo-4-ethyl-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3',4’:6,7]indolizino[1,2-b]quinolin-4-yl]oxy}-2-oxoethyl)cyclohexyl]methyl}-N⁵-carbamoyl-L-ornithinamide; With dmap; In tetrahydrofuran; at 20 ℃; for 0.333333h;

Reference yield:

L-valyl-N-{[1-(2-{[(4S)-10-bromo-4-ethyl-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3',4’:6,7]indolizino[1,2-b]quinolin-4-yl]oxy}-2-oxoethyl)cyclohexyl]methyl}-N5-carbamoyl-L-ornithinamide (1609075-27-5) → N-[6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoyl]-L-valyl-N-{4-[({[4-({[(4S)-1-bromo-4-ethyl-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3’,4’:6,7]indol izino[1,2-b]quinolin-4-yl]oxy}carbonyl)piperazin-1-yl]carbonyl}oxy)methyl]phenyl}-N5-carbamoyl-L-ornithinamide (1609075-05-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: dicyclohexyl-carbodiimide; benzotriazol-1-ol / tetrahydrofuran / 3 h / 20 °C

1.2: 0.33 h / 20 °C

2.1: diethylenetriaminopentaacetic acid; sodium chloride / aq. buffer / 1 h / 21 °C

3.1: cathepsin B / aq. buffer / 20 - 40 °C

4.1: tetrahydrofuran / 5 h / 55 °C

5.1: acetonitrile / 1.5 h / 20 °C

6.1: dimethyl sulfoxide / 2 h / 20 °C

With diethylenetriaminopentaacetic acid; benzotriazol-1-ol; dicyclohexyl-carbodiimide; sodium chloride; cathepsin B; In tetrahydrofuran; dimethyl sulfoxide; acetonitrile;

Downstream raw materials:

N-[6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoyl]-L-valyl-N-{4-[({[4-({[(4S)-1-bromo-4-ethyl-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3’,4’:6,7]indol izino[1,2-b]quinolin-4-yl]oxy}carbonyl)piperazin-1-yl]carbonyl}oxy)methyl]phenyl}-N⁵-carbamoyl-L-ornithinamide

(4S)-10-bromo-4-ethyl-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-4-yl L-phenylalanyl-L-leucylglycinate

(4S)-10-bromo-4-ethyl-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3',4':6,7]indolizino[1 ,2-b]quinolin-4-yl N-[6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoyl]-L-phenylalanyl-L-leucylglycinate

(4S)-10-bromo-4-ethyl-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-4-yl (1-{[(tertbutoxycarbonyl)amino]methyl}cyclohexyl)acetate

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