2-(2-tert-butoxycarbonylamino-benzoylamino)-4-{1-tert-butoxycarbonyl-3-[1-tert-butoxycarbonyl-2-(4-hydroxy-3-nitro-phenyl)-ethylcarbamoyl]-propylcarbamoyl}-4,4-difluoro-butyric acid tert-butyl ester

Base Information

• Chemical Name: 2-(2-tert-butoxycarbonylamino-benzoylamino)-4-{1-tert-butoxycarbonyl-3-[1-tert-butoxycarbonyl-2-(4-hydroxy-3-nitro-phenyl)-ethylcarbamoyl]-propylcarbamoyl}-4,4-difluoro-butyric acid tert-butyl ester
• CAS No.: 510714-05-3
• Molecular Formula: C₄₃H₅₉F₂N₅O₁₄
• Molecular Weight: 907.963

Synonyms:2-(2-tert-butoxycarbonylamino-benzoylamino)-4-{1-tert-butoxycarbonyl-3-[1-tert-butoxycarbonyl-2-(4-hydroxy-3-nitro-phenyl)-ethylcarbamoyl]-propylcarbamoyl}-4,4-difluoro-butyric acid tert-butyl ester

Chemical Property of 2-(2-tert-butoxycarbonylamino-benzoylamino)-4-{1-tert-butoxycarbonyl-3-[1-tert-butoxycarbonyl-2-(4-hydroxy-3-nitro-phenyl)-ethylcarbamoyl]-propylcarbamoyl}-4,4-difluoro-butyric acid tert-butyl ester

Chemical Property:

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Technology Process of 2-(2-tert-butoxycarbonylamino-benzoylamino)-4-{1-tert-butoxycarbonyl-3-[1-tert-butoxycarbonyl-2-(4-hydroxy-3-nitro-phenyl)-ethylcarbamoyl]-propylcarbamoyl}-4,4-difluoro-butyric acid tert-butyl ester

There total 14 articles about 2-(2-tert-butoxycarbonylamino-benzoylamino)-4-{1-tert-butoxycarbonyl-3-[1-tert-butoxycarbonyl-2-(4-hydroxy-3-nitro-phenyl)-ethylcarbamoyl]-propylcarbamoyl}-4,4-difluoro-butyric 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:

N-(benzyloxycarbonyl)-L-glutamic acid α-t-butyl ester dicyclohexylamine salt (34897-61-5) → 2-(2-tert-butoxycarbonylamino-benzoylamino)-4-{1-tert-butoxycarbonyl-3-[1-tert-butoxycarbonyl-2-(4-hydroxy-3-nitro-phenyl)-ethylcarbamoyl]-propylcarbamoyl}-4,4-difluoro-butyric acid tert-butyl ester (510714-05-3)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 86 percent / DMAP; EDC / CH₂Cl₂ / 36 h / 20 °C

2.1: H₂ / 10 percent Pd/C / methanol; propan-2-ol / 1.5 h / 2068.59 Torr

3.1: aq. NaOH / tetrahydrofuran / 1 h / 0 °C

3.2: 402 mg / HOBt; DCC / dimethylformamide; CH₂Cl₂ / 48 h / 20 °C

4.1: 65 percent / aq. TsOH / acetonitrile / 19 h / 20 °C

5.1: H₅IO₆; CrO₃; H₂O / acetonitrile / 1.5 h / 0 °C

6.1: 47 mg / CH₂Cl₂ / 36 h / 20 °C

7.1: H₂ / 10 percent Pd/C / tetrahydrofuran / 1 h / 0 °C / 760 Torr

8.1: 44 mg / HOBt; DCC / dimethylformamide / 96 h / 20 °C

9.1: TBAF / tetrahydrofuran / 2 h / 0 °C

10.1: 44 mg / HOBt; DCC / dimethylformamide / 48 h / 20 °C

With chromium(VI) oxide; dmap; sodium hydroxide; tetrabutyl ammonium fluoride; water; hydrogen; benzotriazol-1-ol; toluene-4-sulfonic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; periodic acid; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; acetonitrile;

DOI:10.1055/s-2002-35616

Reference yield:

N-Cbz-L-glutamic acid α-tert-butyl ester γ-(2-trimethylsilyl)ethyl ester (357958-50-0) → 2-(2-tert-butoxycarbonylamino-benzoylamino)-4-{1-tert-butoxycarbonyl-3-[1-tert-butoxycarbonyl-2-(4-hydroxy-3-nitro-phenyl)-ethylcarbamoyl]-propylcarbamoyl}-4,4-difluoro-butyric acid tert-butyl ester (510714-05-3)

Guidance literature:

Multi-step reaction with 9 steps

1.1: H₂ / 10 percent Pd/C / methanol; propan-2-ol / 1.5 h / 2068.59 Torr

2.1: aq. NaOH / tetrahydrofuran / 1 h / 0 °C

2.2: 402 mg / HOBt; DCC / dimethylformamide; CH₂Cl₂ / 48 h / 20 °C

3.1: 65 percent / aq. TsOH / acetonitrile / 19 h / 20 °C

4.1: H₅IO₆; CrO₃; H₂O / acetonitrile / 1.5 h / 0 °C

5.1: 47 mg / CH₂Cl₂ / 36 h / 20 °C

6.1: H₂ / 10 percent Pd/C / tetrahydrofuran / 1 h / 0 °C / 760 Torr

7.1: 44 mg / HOBt; DCC / dimethylformamide / 96 h / 20 °C

8.1: TBAF / tetrahydrofuran / 2 h / 0 °C

9.1: 44 mg / HOBt; DCC / dimethylformamide / 48 h / 20 °C

With chromium(VI) oxide; sodium hydroxide; tetrabutyl ammonium fluoride; water; hydrogen; benzotriazol-1-ol; toluene-4-sulfonic acid; periodic acid; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; acetonitrile;

DOI:10.1055/s-2002-35616

Reference yield:

H-Glu(α-OtBu)(γ-OTMSE) (510713-97-0) → 2-(2-tert-butoxycarbonylamino-benzoylamino)-4-{1-tert-butoxycarbonyl-3-[1-tert-butoxycarbonyl-2-(4-hydroxy-3-nitro-phenyl)-ethylcarbamoyl]-propylcarbamoyl}-4,4-difluoro-butyric acid tert-butyl ester (510714-05-3)

Guidance literature:

Multi-step reaction with 8 steps

1.1: aq. NaOH / tetrahydrofuran / 1 h / 0 °C

1.2: 402 mg / HOBt; DCC / dimethylformamide; CH₂Cl₂ / 48 h / 20 °C

2.1: 65 percent / aq. TsOH / acetonitrile / 19 h / 20 °C

3.1: H₅IO₆; CrO₃; H₂O / acetonitrile / 1.5 h / 0 °C

4.1: 47 mg / CH₂Cl₂ / 36 h / 20 °C

5.1: H₂ / 10 percent Pd/C / tetrahydrofuran / 1 h / 0 °C / 760 Torr

6.1: 44 mg / HOBt; DCC / dimethylformamide / 96 h / 20 °C

7.1: TBAF / tetrahydrofuran / 2 h / 0 °C

8.1: 44 mg / HOBt; DCC / dimethylformamide / 48 h / 20 °C

With chromium(VI) oxide; sodium hydroxide; tetrabutyl ammonium fluoride; water; hydrogen; benzotriazol-1-ol; toluene-4-sulfonic acid; periodic acid; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1055/s-2002-35616

upstream raw materials:

2-(tert-butyloxycarbonylamino)benzoic acid

N-(benzyloxycarbonyl)-L-glutamic acid α-t-butyl ester dicyclohexylamine salt

H-Glu(α-OtBu)(γ-OTMSE)

N-Cbz-L-glutamic acid α-tert-butyl ester γ-(2-trimethylsilyl)ethyl ester

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