{4-[(5-mercaptocarbonimidoyl-benzo[b]thiophene-2-carbonyl)-amino]-phenoxy}-acetic acid tert-butyl ester

Base Information

• Chemical Name: {4-[(5-mercaptocarbonimidoyl-benzo[b]thiophene-2-carbonyl)-amino]-phenoxy}-acetic acid tert-butyl ester
• CAS No.: 1026500-69-5
• Molecular Formula: C₂₂H₂₂N₂O₄S₂
• Molecular Weight: 442.56

Synonyms:{4-[(5-mercaptocarbonimidoyl-benzo[b]thiophene-2-carbonyl)-amino]-phenoxy}-acetic acid tert-butyl ester

Chemical Property of {4-[(5-mercaptocarbonimidoyl-benzo[b]thiophene-2-carbonyl)-amino]-phenoxy}-acetic acid tert-butyl ester

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Technology Process of {4-[(5-mercaptocarbonimidoyl-benzo[b]thiophene-2-carbonyl)-amino]-phenoxy}-acetic acid tert-butyl ester

There total 5 articles about {4-[(5-mercaptocarbonimidoyl-benzo[b]thiophene-2-carbonyl)-amino]-phenoxy}-acetic acid tert-butyl 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: 41.0%

t-butyl 4-[(5-cyanobenzo [b]thien-2-yl)carbonylamino]phenoxyacetate (174774-80-2) → {4-[(5-mercaptocarbonimidoyl-benzo[b]thiophene-2-carbonyl)-amino]-phenoxy}-acetic acid tert-butyl ester (1026500-69-5)

Guidance literature:

With TEA; hydrogen sulfide; In pyridine; at 20 ℃; for 18h;

DOI:10.1248/cpb.47.1694

Reference yield:

ethyl 5-nitro-2-benzo[b]thiophenecarboxylate (25785-09-5) → {4-[(5-mercaptocarbonimidoyl-benzo[b]thiophene-2-carbonyl)-amino]-phenoxy}-acetic acid tert-butyl ester (1026500-69-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: H₂ / 10 percent Pd/C / ethanol / 15 h / 20 °C

2.1: 12N aq. HCl; NaNO₂ / tetrahydrofuran / 0.33 h / 2 - 3 °C

2.2: KCN / 3.5 h / 3 - 50 °C

3.1: 100 percent / aq. LiOH / tetrahydrofuran / 1 h / 20 °C

4.1: 85 percent / HOBt; EDI / dimethylformamide / 18 h / 20 °C

5.1: 41 percent / H₂S; TEA / pyridine / 18 h / 20 °C

With hydrogenchloride; lithium hydroxide; TEA; hydrogen sulfide; hydrogen; benzotriazol-1-ol; sodium nitrite; palladium on activated charcoal; In tetrahydrofuran; pyridine; ethanol; N,N-dimethyl-formamide; 1.1: Reduction / 2.1: Diazotization / 2.2: Sandmeyer reaction / 3.1: Hydrolysis / 4.1: coupling / 5.1: Addition;

DOI:10.1248/cpb.47.1694

Reference yield:

ethyl 5-amino-1-benzothiophene-2-carboxylate (25785-10-8) → {4-[(5-mercaptocarbonimidoyl-benzo[b]thiophene-2-carbonyl)-amino]-phenoxy}-acetic acid tert-butyl ester (1026500-69-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 12N aq. HCl; NaNO₂ / tetrahydrofuran / 0.33 h / 2 - 3 °C

1.2: KCN / 3.5 h / 3 - 50 °C

2.1: 100 percent / aq. LiOH / tetrahydrofuran / 1 h / 20 °C

3.1: 85 percent / HOBt; EDI / dimethylformamide / 18 h / 20 °C

4.1: 41 percent / H₂S; TEA / pyridine / 18 h / 20 °C

With hydrogenchloride; lithium hydroxide; TEA; hydrogen sulfide; benzotriazol-1-ol; sodium nitrite; In tetrahydrofuran; pyridine; N,N-dimethyl-formamide; 1.1: Diazotization / 1.2: Sandmeyer reaction / 2.1: Hydrolysis / 3.1: coupling / 4.1: Addition;

DOI:10.1248/cpb.47.1694

upstream raw materials:

t-butyl 4-[(5-cyanobenzo [b]thien-2-yl)carbonylamino]phenoxyacetate

ethyl 5-amino-1-benzothiophene-2-carboxylate

ethyl 5-nitro-2-benzo[b]thiophenecarboxylate

5-Cyanbenzothiophen-2-carbonsaeure-ethylester

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