4-[(7-{2-benzyloxy-5-[2-benzyloxycarbonylamino-2-(1-tert-butoxycarbonyl-2-carbamoyl-ethylcarbamoyl)-ethyl]-phenyl}-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)-hydroxy-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: 4-[(7-{2-benzyloxy-5-[2-benzyloxycarbonylamino-2-(1-tert-butoxycarbonyl-2-carbamoyl-ethylcarbamoyl)-ethyl]-phenyl}-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)-hydroxy-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
• CAS No.: 421556-72-1
• Molecular Formula: C₅₁H₆₁N₅O₁₃
• Molecular Weight: 952.071

Synonyms:4-[(7-{2-benzyloxy-5-[2-benzyloxycarbonylamino-2-(1-tert-butoxycarbonyl-2-carbamoyl-ethylcarbamoyl)-ethyl]-phenyl}-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)-hydroxy-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Chemical Property of 4-[(7-{2-benzyloxy-5-[2-benzyloxycarbonylamino-2-(1-tert-butoxycarbonyl-2-carbamoyl-ethylcarbamoyl)-ethyl]-phenyl}-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)-hydroxy-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of 4-[(7-{2-benzyloxy-5-[2-benzyloxycarbonylamino-2-(1-tert-butoxycarbonyl-2-carbamoyl-ethylcarbamoyl)-ethyl]-phenyl}-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)-hydroxy-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

There total 18 articles about 4-[(7-{2-benzyloxy-5-[2-benzyloxycarbonylamino-2-(1-tert-butoxycarbonyl-2-carbamoyl-ethylcarbamoyl)-ethyl]-phenyl}-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)-hydroxy-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic 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: 88.0%

(S)-4-[7-{2-Benzyloxy-5-[(S)-2-benzyloxycarbonylamino-2-((S)-1-tert-butoxycarbonyl-2-carbamoyl-ethylcarbamoyl)-ethyl]-phenyl}-2-oxo-1,2-dihydro-indol-(3E)-ylidenemethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (421556-71-0) → 4-[(7-{2-benzyloxy-5-[2-benzyloxycarbonylamino-2-(1-tert-butoxycarbonyl-2-carbamoyl-ethylcarbamoyl)-ethyl]-phenyl}-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)-hydroxy-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester + 4-[(7-{2-benzyloxy-5-[2-benzyloxycarbonylamino-2-(1-tert-butoxycarbonyl-2-carbamoyl-ethylcarbamoyl)-ethyl]-phenyl}-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)-hydroxy-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (421556-72-1)

Guidance literature:

With (3a,9R,3'''a,4'"b,9'"R)-9,9'-[1,4-phthalazinediylbis(oxy)]bis[6'-(methyloxy)-10,11-dihydrocinchonan]; osmium(VIII) oxide; N-methyl-2-indolinone; In water; tert-butyl alcohol; at 20 ℃; for 12h;

DOI:10.1002/1521-3773(20020201)41:3<512::AID-ANIE512>3.0.CO;2-R

Reference yield:

7-iodooxindole (31676-49-0) → 4-[(7-{2-benzyloxy-5-[2-benzyloxycarbonylamino-2-(1-tert-butoxycarbonyl-2-carbamoyl-ethylcarbamoyl)-ethyl]-phenyl}-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)-hydroxy-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (421556-72-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: LDA / tetrahydrofuran; hexane / 2 h / -78 °C

1.2: 45 percent / Et₃N; MsCl / CH₂Cl₂ / 1.33 h / -75 - -50 °C

2.1: 65 percent / K₂CO₃; [PdCl₂(dppf)]*CH₂Cl₂ / 1,2-dimethoxy-ethane / 5 h / 80 °C

3.1: aq. LiOH / tetrahydrofuran / 2.5 h / 0 °C

4.1: 85 percent / 1-hydroxy-7-azabenzotriazole; 1-[3-dimethylaminopropyl]-3-ethylcarbodiimide hydrochloride / tetrahydrofuran / 2.5 h / 20 °C

5.1: OsO₄; 4-methylmorpholine N-oxide; 1,4-bis(9-O-dihydroquinidine)phthalazine / 2-methyl-propan-2-ol; H₂O / 14 h / 20 °C

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; (3a,9R,3'''a,4'"b,9'"R)-9,9'-[1,4-phthalazinediylbis(oxy)]bis[6'-(methyloxy)-10,11-dihydrocinchonan]; lithium hydroxide; osmium(VIII) oxide; 1-hydroxy-7-aza-benzotriazole; potassium carbonate; 4-methylmorpholine N-oxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium diisopropyl amide; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; water; tert-butyl alcohol; 2.1: Suzuki coupling;

DOI:10.1021/ja049821k

Reference yield:

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine (95715-87-0) → 4-[(7-{2-benzyloxy-5-[2-benzyloxycarbonylamino-2-(1-tert-butoxycarbonyl-2-carbamoyl-ethylcarbamoyl)-ethyl]-phenyl}-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)-hydroxy-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (421556-72-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: LDA / tetrahydrofuran; hexane / 2 h / -78 °C

1.2: 45 percent / Et₃N; MsCl / CH₂Cl₂ / 1.33 h / -75 - -50 °C

2.1: 65 percent / K₂CO₃; [PdCl₂(dppf)]*CH₂Cl₂ / 1,2-dimethoxy-ethane / 5 h / 80 °C

3.1: aq. LiOH / tetrahydrofuran / 2.5 h / 0 °C

4.1: 85 percent / 1-hydroxy-7-azabenzotriazole; 1-[3-dimethylaminopropyl]-3-ethylcarbodiimide hydrochloride / tetrahydrofuran / 2.5 h / 20 °C

5.1: OsO₄; 4-methylmorpholine N-oxide; 1,4-bis(9-O-dihydroquinidine)phthalazine / 2-methyl-propan-2-ol; H₂O / 14 h / 20 °C

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; (3a,9R,3'''a,4'"b,9'"R)-9,9'-[1,4-phthalazinediylbis(oxy)]bis[6'-(methyloxy)-10,11-dihydrocinchonan]; lithium hydroxide; osmium(VIII) oxide; 1-hydroxy-7-aza-benzotriazole; potassium carbonate; 4-methylmorpholine N-oxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium diisopropyl amide; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; water; tert-butyl alcohol; 2.1: Suzuki coupling;

DOI:10.1021/ja049821k

upstream raw materials:

(S)-4-[7-{2-Benzyloxy-5-[(S)-2-benzyloxycarbonylamino-2-((S)-1-tert-butoxycarbonyl-2-carbamoyl-ethylcarbamoyl)-ethyl]-phenyl}-2-oxo-1,2-dihydro-indol-(3E)-ylidenemethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

7-iodoisatin

7-iodooxindole

2-iodophenylamine

Downstream raw materials:

TMC-95B

2-(3-{4-benzyloxy-3-[3-(2-tert-butoxycarbonylamino-1-hydroxy-3-triisopropylsilanyloxy-propyl)-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-7-yl]-phenyl}-2-benzyloxycarbonylamino-propionylamino)-succinamic acid tert-butyl ester

TMC-95A

2-(3-{4-benzyloxy-3-[3-(2-tert-butoxycarbonylamino-1,3-dihydroxy-propyl)-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-7-yl]-phenyl}-2-benzyloxycarbonylamino-propionylamino)-succinamic acid tert-butyl ester

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