4-(2-acetylamino-3-tert-butoxycarbonyl-propionylamino)-4-(1-{1-[2-cyclohexyl-1-(1-ethyl-2-oxo-4-phenyl-but-3-enylcarbamoyl)-ethylcarbamoyl]-2-methyl-butylcarbamoyl}-3-methyl-butylcarbamoyl)-butyric acid tert-butyl ester

Base Information

• Chemical Name: 4-(2-acetylamino-3-tert-butoxycarbonyl-propionylamino)-4-(1-{1-[2-cyclohexyl-1-(1-ethyl-2-oxo-4-phenyl-but-3-enylcarbamoyl)-ethylcarbamoyl]-2-methyl-butylcarbamoyl}-3-methyl-butylcarbamoyl)-butyric acid tert-butyl ester
• CAS No.: 622841-17-2
• Molecular Formula: C₅₂H₈₂N₆O₁₁
• Molecular Weight: 967.257

Synonyms:4-(2-acetylamino-3-tert-butoxycarbonyl-propionylamino)-4-(1-{1-[2-cyclohexyl-1-(1-ethyl-2-oxo-4-phenyl-but-3-enylcarbamoyl)-ethylcarbamoyl]-2-methyl-butylcarbamoyl}-3-methyl-butylcarbamoyl)-butyric acid tert-butyl ester

Chemical Property of 4-(2-acetylamino-3-tert-butoxycarbonyl-propionylamino)-4-(1-{1-[2-cyclohexyl-1-(1-ethyl-2-oxo-4-phenyl-but-3-enylcarbamoyl)-ethylcarbamoyl]-2-methyl-butylcarbamoyl}-3-methyl-butylcarbamoyl)-butyric acid tert-butyl ester

Chemical Property:

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Technology Process of 4-(2-acetylamino-3-tert-butoxycarbonyl-propionylamino)-4-(1-{1-[2-cyclohexyl-1-(1-ethyl-2-oxo-4-phenyl-but-3-enylcarbamoyl)-ethylcarbamoyl]-2-methyl-butylcarbamoyl}-3-methyl-butylcarbamoyl)-butyric acid tert-butyl ester

There total 7 articles about 4-(2-acetylamino-3-tert-butoxycarbonyl-propionylamino)-4-(1-{1-[2-cyclohexyl-1-(1-ethyl-2-oxo-4-phenyl-but-3-enylcarbamoyl)-ethylcarbamoyl]-2-methyl-butylcarbamoyl}-3-methyl-butylcarbamoyl)-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:

Fmoc-Ile-OH (71989-23-6,251316-98-0) → 4-(2-acetylamino-3-tert-butoxycarbonyl-propionylamino)-4-(1-{1-[2-cyclohexyl-1-(1-ethyl-2-oxo-4-phenyl-but-3-enylcarbamoyl)-ethylcarbamoyl]-2-methyl-butylcarbamoyl}-3-methyl-butylcarbamoyl)-butyric acid tert-butyl ester (622841-17-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 151 mg / PyBOP; DIPEA / CH₂Cl₂ / 16 h

2: 69 percent / Dess-Martin reagent / CH₂Cl₂ / 16 h / 20 °C

With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; In dichloromethane; 3: Dess-Martin oxidation;

DOI:10.1016/S0968-0896(03)00190-1

Reference yield:

benzaldehyde (100-52-7) → 4-(2-acetylamino-3-tert-butoxycarbonyl-propionylamino)-4-(1-{1-[2-cyclohexyl-1-(1-ethyl-2-oxo-4-phenyl-but-3-enylcarbamoyl)-ethylcarbamoyl]-2-methyl-butylcarbamoyl}-3-methyl-butylcarbamoyl)-butyric acid tert-butyl ester (622841-17-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / K₂CO₃ / ethanol / 16 h

2: 96 percent / NaBH₄ / methanol / 2.5 h / 0 °C

3: TMSOTf; 2,6-lutidine / CH₂Cl₂ / 6 h

4: 151 mg / PyBOP; DIPEA / CH₂Cl₂ / 16 h

5: 69 percent / Dess-Martin reagent / CH₂Cl₂ / 16 h / 20 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; trimethylsilyl trifluoromethanesulfonate; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; potassium carbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; In methanol; ethanol; dichloromethane; 1: Horner-Wadsworth-Emmons reaction / 5: Dess-Martin oxidation;

DOI:10.1016/S0968-0896(03)00190-1

Reference yield:

(E)-(S)-4-Amino-1-phenyl-hex-1-en-3-ol → 4-(2-acetylamino-3-tert-butoxycarbonyl-propionylamino)-4-(1-{1-[2-cyclohexyl-1-(1-ethyl-2-oxo-4-phenyl-but-3-enylcarbamoyl)-ethylcarbamoyl]-2-methyl-butylcarbamoyl}-3-methyl-butylcarbamoyl)-butyric acid tert-butyl ester (622841-17-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 151 mg / PyBOP; DIPEA / CH₂Cl₂ / 16 h

2: 69 percent / Dess-Martin reagent / CH₂Cl₂ / 16 h / 20 °C

With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; In dichloromethane; 2: Dess-Martin oxidation;

DOI:10.1016/S0968-0896(03)00190-1

upstream raw materials:

Fmoc-Ile-OH

benzaldehyde

((E)-(S)-1-Ethyl-2-oxo-4-phenyl-but-3-enyl)-carbamic acid tert-butyl ester

((E)-(S)-1-Ethyl-2-hydroxy-4-phenyl-but-3-enyl)-carbamic acid tert-butyl ester

Downstream raw materials:

(R)-4-((S)-2-Acetylamino-3-tert-butoxycarbonyl-propionylamino)-4-((S)-1-{(1S,2S)-1-[(S)-2-cyclohexyl-1-((S)-1-ethyl-2-oxo-4-phenyl-butylcarbamoyl)-ethylcarbamoyl]-2-methyl-butylcarbamoyl}-3-methyl-butylcarbamoyl)-butyric acid tert-butyl ester

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