(2S,3R)-3-((S)-4-tert-Butoxycarbonylamino-1-methylcarbamoyl-butylcarbamoyl)-2-hydroxy-6-phenyl-2-trifluoromethyl-hexanoic acid ethyl ester

Base Information

• Chemical Name: (2S,3R)-3-((S)-4-tert-Butoxycarbonylamino-1-methylcarbamoyl-butylcarbamoyl)-2-hydroxy-6-phenyl-2-trifluoromethyl-hexanoic acid ethyl ester
• CAS No.: 679437-25-3
• Molecular Formula: C₂₇H₄₀F₃N₃O₇
• Molecular Weight: 575.626

Synonyms:(2S,3R)-3-((S)-4-tert-Butoxycarbonylamino-1-methylcarbamoyl-butylcarbamoyl)-2-hydroxy-6-phenyl-2-trifluoromethyl-hexanoic acid ethyl ester

Chemical Property of (2S,3R)-3-((S)-4-tert-Butoxycarbonylamino-1-methylcarbamoyl-butylcarbamoyl)-2-hydroxy-6-phenyl-2-trifluoromethyl-hexanoic acid ethyl ester

Chemical Property:

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Technology Process of (2S,3R)-3-((S)-4-tert-Butoxycarbonylamino-1-methylcarbamoyl-butylcarbamoyl)-2-hydroxy-6-phenyl-2-trifluoromethyl-hexanoic acid ethyl ester

There total 4 articles about (2S,3R)-3-((S)-4-tert-Butoxycarbonylamino-1-methylcarbamoyl-butylcarbamoyl)-2-hydroxy-6-phenyl-2-trifluoromethyl-hexanoic acid ethyl 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: 68.0%

N-δ-tert-butoxycarbonyl-L-ornithine methyl amide (178932-85-9) + (2S,3R)-2-Hydroxy-3-(3-phenyl-propyl)-2-trifluoromethyl-succinic acid 1-ethyl ester (679437-21-9) → (2S,3R)-3-((S)-4-tert-Butoxycarbonylamino-1-methylcarbamoyl-butylcarbamoyl)-2-hydroxy-6-phenyl-2-trifluoromethyl-hexanoic acid ethyl ester (679437-25-3)

Guidance literature:

With 1-hydroxy-7-aza-benzotriazole; thymidine 5'-phosphate; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; for 2h;

DOI:10.1016/j.tet.2006.08.036

Reference yield:

ethyl-3,3,3-trifluoropyruvate (13081-18-0) → (2S,3R)-3-((S)-4-tert-Butoxycarbonylamino-1-methylcarbamoyl-butylcarbamoyl)-2-hydroxy-6-phenyl-2-trifluoromethyl-hexanoic acid ethyl ester (679437-25-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: TiCl₄; DIPEA / CH₂Cl₂; toluene / 0.33 h / 0 °C

1.2: 59 mg / CH₂Cl₂; toluene / -70 - 20 °C

2.1: 71 percent / potassium carbonate / dioxane; H₂O / 10 h

3.1: 68 percent / HOAt; HATU; TMP / dimethylformamide / 2 h

With 1-hydroxy-7-aza-benzotriazole; titanium tetrachloride; potassium carbonate; thymidine 5'-phosphate; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.tet.2006.08.036

Reference yield:

1-((S)-4-Benzyl-2-thioxo-oxazolidin-3-yl)-5-phenyl-pentan-1-one → (2S,3R)-3-((S)-4-tert-Butoxycarbonylamino-1-methylcarbamoyl-butylcarbamoyl)-2-hydroxy-6-phenyl-2-trifluoromethyl-hexanoic acid ethyl ester (679437-25-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: TiCl₄; DIPEA / CH₂Cl₂; toluene / 0.33 h / 0 °C

1.2: 59 mg / CH₂Cl₂; toluene / -70 - 20 °C

2.1: 71 percent / potassium carbonate / dioxane; H₂O / 10 h

3.1: 68 percent / HOAt; HATU; TMP / dimethylformamide / 2 h

With 1-hydroxy-7-aza-benzotriazole; titanium tetrachloride; potassium carbonate; thymidine 5'-phosphate; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.tet.2006.08.036

upstream raw materials:

N-δ-tert-butoxycarbonyl-L-ornithine methyl amide

(2S,3R)-2-Hydroxy-3-(3-phenyl-propyl)-2-trifluoromethyl-succinic acid 1-ethyl ester

ethyl-3,3,3-trifluoropyruvate

(2S,3R)-3-((S)-4-Benzyl-2-thioxo-oxazolidine-3-carbonyl)-2-hydroxy-6-phenyl-2-trifluoromethyl-hexanoic acid ethyl ester

Downstream raw materials:

{(S)-4-[(R)-2-((S)-1-Benzyloxycarbamoyl-2,2,2-trifluoro-1-hydroxy-ethyl)-5-phenyl-pentanoylamino]-4-methylcarbamoyl-butyl}-carbamic acid tert-butyl ester

(2S,3R)-3-((S)-4-tert-Butoxycarbonylamino-1-methylcarbamoyl-butylcarbamoyl)-2-hydroxy-6-phenyl-2-trifluoromethyl-hexanoic acid

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