(1'R,2''S,3''R,4''S)-2-<1--2-(4-thiazolyl)ethyl>-1,2,3,4-tetrahydropyrrolo<3,4-b>indol-3-one

Base Information

• Chemical Name: (1'R,2''S,3''R,4''S)-2-<1--2-(4-thiazolyl)ethyl>-1,2,3,4-tetrahydropyrrolo<3,4-b>indol-3-one
• CAS No.: 124223-57-0
• Molecular Formula: C₃₀H₄₀N₄O₄S
• Molecular Weight: 552.738

Synonyms:

Chemical Property of (1'R,2''S,3''R,4''S)-2-<1--2-(4-thiazolyl)ethyl>-1,2,3,4-tetrahydropyrrolo<3,4-b>indol-3-one

Chemical Property:

Purity/Quality:

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Technology Process of (1'R,2''S,3''R,4''S)-2-<1--2-(4-thiazolyl)ethyl>-1,2,3,4-tetrahydropyrrolo<3,4-b>indol-3-one

There total 3 articles about (1'R,2''S,3''R,4''S)-2-<1--2-(4-thiazolyl)ethyl>-1,2,3,4-tetrahydropyrrolo<3,4-b>indol-3-one 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:

N-<<3-<2-(benzyloxycarbonyl)indolyl>>methyl>-dl-β-4-thiazolylalanine methyl ester (124156-43-0) → (1'R,2''S,3''R,4''S)-2-<1--2-(4-thiazolyl)ethyl>-1,2,3,4-tetrahydropyrrolo<3,4-b>indol-3-one (124223-57-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 8.5 g / HBr / acetic acid / 3.25 h / Ambient temperature

2: 86 percent / 4-(dimethylamino)pyridine, 4-methylmorpholine, N-ethyl-N'-<2-(dimethylamino)ethyl>carbodiimide / dimethylformamide / 16 h / Ambient temperature

3: 1.) LiOH 2.) 1-hydroxybenzotriazole, N-ethyl-N'-<3-(diethylamino)propyl>carbodiimide, 4-methylmorpholine / 1.) 1,4-dioxane, 0 deg C, 3.5h 2.) DMF, -23 deg C -> r. t. overnight

With 4-methyl-morpholine; dmap; lithium hydroxide; N-ethyl-N'-(3-diethylaminopropyl)-carbodiimide; hydrogen bromide; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In acetic acid; N,N-dimethyl-formamide;

DOI:10.1021/jo00291a060

Reference yield:

3-[(1-Methoxycarbonyl-1-thiazol-4-yl-ethylamino)-methyl]-1H-indole-2-carboxylic acid; hydrobromide → (1'R,2''S,3''R,4''S)-2-<1--2-(4-thiazolyl)ethyl>-1,2,3,4-tetrahydropyrrolo<3,4-b>indol-3-one (124223-57-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / 4-(dimethylamino)pyridine, 4-methylmorpholine, N-ethyl-N'-<2-(dimethylamino)ethyl>carbodiimide / dimethylformamide / 16 h / Ambient temperature

2: 1.) LiOH 2.) 1-hydroxybenzotriazole, N-ethyl-N'-<3-(diethylamino)propyl>carbodiimide, 4-methylmorpholine / 1.) 1,4-dioxane, 0 deg C, 3.5h 2.) DMF, -23 deg C -> r. t. overnight

With 4-methyl-morpholine; dmap; lithium hydroxide; N-ethyl-N'-(3-diethylaminopropyl)-carbodiimide; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In N,N-dimethyl-formamide;

DOI:10.1021/jo00291a060

Reference yield:

2-<1-(methoxycarbonyl)-2-(4-thiazolyl)ethyl>-1,2,3,4-tetrahydropyrrolo<3,4-b>indole-3-one (124175-17-3) + (S)-2-amino-1-cyclohexyl-(R)-3,(S)-4-dihydroxy-6-methylheptane hydrochloride (104882-45-3) → (1'R,2''S,3''R,4''S)-2-<1--2-(4-thiazolyl)ethyl>-1,2,3,4-tetrahydropyrrolo<3,4-b>indol-3-one (124223-57-0) + (1'S,2''S,3''R,4''S)-2-<1--2-(4-thiazolyl)ethyl>-1,2,3,4-tetrahydropyrrolo<3,4-b>indol-3-one (124156-56-5)

Guidance literature:

With 4-methyl-morpholine; lithium hydroxide; N-ethyl-N'-(3-diethylaminopropyl)-carbodiimide; benzotriazol-1-ol; Yield given. Yields of byproduct given; 1.) 1,4-dioxane, 0 deg C, 3.5h 2.) DMF, -23 deg C -> r. t. overnight;

DOI:10.1021/jo00291a060

upstream raw materials:

2-<1-(methoxycarbonyl)-2-(4-thiazolyl)ethyl>-1,2,3,4-tetrahydropyrrolo<3,4-b>indole-3-one

(S)-2-amino-1-cyclohexyl-(R)-3,(S)-4-dihydroxy-6-methylheptane hydrochloride

N-<<3-<2-(benzyloxycarbonyl)indolyl>>methyl>-dl-β-4-thiazolylalanine methyl ester

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