N¹-benzyloxy-N⁴-(2,2-dimethyl-1-methylcarbamoyl-propyl)-2-hydroxy-3-(3-phenyl-propyl)-2-trifluoromethyl-succinamide

Base Information

• Chemical Name: N¹-benzyloxy-N⁴-(2,2-dimethyl-1-methylcarbamoyl-propyl)-2-hydroxy-3-(3-phenyl-propyl)-2-trifluoromethyl-succinamide
• CAS No.: 679437-29-7
• Molecular Formula: C₂₈H₃₆F₃N₃O₅
• Molecular Weight: 551.606

Synonyms:N¹-benzyloxy-N⁴-(2,2-dimethyl-1-methylcarbamoyl-propyl)-2-hydroxy-3-(3-phenyl-propyl)-2-trifluoromethyl-succinamide

Chemical Property of N¹-benzyloxy-N⁴-(2,2-dimethyl-1-methylcarbamoyl-propyl)-2-hydroxy-3-(3-phenyl-propyl)-2-trifluoromethyl-succinamide

Chemical Property:

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Technology Process of N¹-benzyloxy-N⁴-(2,2-dimethyl-1-methylcarbamoyl-propyl)-2-hydroxy-3-(3-phenyl-propyl)-2-trifluoromethyl-succinamide

There total 6 articles about N¹-benzyloxy-N⁴-(2,2-dimethyl-1-methylcarbamoyl-propyl)-2-hydroxy-3-(3-phenyl-propyl)-2-trifluoromethyl-succinamide 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: 61.0%

N-benzyloxyamine (622-33-3) + (2S,3R)-3-((S)-2,2-Dimethyl-1-methylcarbamoyl-propylcarbamoyl)-2-hydroxy-6-phenyl-2-trifluoromethyl-hexanoic acid (679437-26-4) → N1-benzyloxy-N4-(2,2-dimethyl-1-methylcarbamoyl-propyl)-2-hydroxy-3-(3-phenyl-propyl)-2-trifluoromethyl-succinamide (679437-29-7)

Guidance literature:

(2S,3R)-3-((S)-2,2-Dimethyl-1-methylcarbamoyl-propylcarbamoyl)-2-hydroxy-6-phenyl-2-trifluoromethyl-hexanoic acid; With diethyl phosphorobromidate; thymidine 5'-phosphate; In dichloromethane; N,N-dimethyl-formamide; at 0 ℃; for 0.75h;

N-benzyloxyamine; With thymidine 5'-phosphate; In dichloromethane; N,N-dimethyl-formamide; at 0 - 20 ℃;

DOI:10.1016/j.tet.2006.08.036

Reference yield:

(S)-2-amino-N,3,3-trimethylbutanamide (89226-12-0) → N1-benzyloxy-N4-(2,2-dimethyl-1-methylcarbamoyl-propyl)-2-hydroxy-3-(3-phenyl-propyl)-2-trifluoromethyl-succinamide (679437-29-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 71 percent / HOAt; HATU; TMP / dimethylformamide / 2 h

2.1: 96 percent / KOH / methanol; H₂O / 2 h

3.1: BrPO(OEt)2; TMP / CH₂Cl₂; dimethylformamide / 0.75 h / 0 °C

3.2: 61 percent / TMP / CH₂Cl₂; dimethylformamide / 0 - 20 °C

With potassium hydroxide; 1-hydroxy-7-aza-benzotriazole; diethyl phosphorobromidate; thymidine 5'-phosphate; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2006.08.036

Reference yield:

1-((S)-4-Benzyl-2-thioxo-oxazolidin-3-yl)-5-phenyl-pentan-1-one → N1-benzyloxy-N4-(2,2-dimethyl-1-methylcarbamoyl-propyl)-2-hydroxy-3-(3-phenyl-propyl)-2-trifluoromethyl-succinamide (679437-29-7)

Guidance literature:

Multi-step reaction with 5 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: 71 percent / HOAt; HATU; TMP / dimethylformamide / 2 h

4.1: 96 percent / KOH / methanol; H₂O / 2 h

5.1: BrPO(OEt)2; TMP / CH₂Cl₂; dimethylformamide / 0.75 h / 0 °C

5.2: 61 percent / TMP / CH₂Cl₂; dimethylformamide / 0 - 20 °C

With potassium hydroxide; 1-hydroxy-7-aza-benzotriazole; diethyl phosphorobromidate; 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; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.tet.2006.08.036

upstream raw materials:

N-benzyloxyamine

(2S,3R)-3-((S)-2,2-Dimethyl-1-methylcarbamoyl-propylcarbamoyl)-2-hydroxy-6-phenyl-2-trifluoromethyl-hexanoic acid

(S)-2-amino-N,3,3-trimethylbutanamide

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

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